


My Brother's Key Keeper

by NinNinNin



Category: Supernatural
Genre: Blowjobs, Bottom Dean, Catheters, Chastity Device, Cock Cage, Drug Use, Emotional Manipulation, I guess???, M/M, Non-Consensual, Non-Consensual Drug Use, Non-Consensual Spanking, Sadistic Sam Winchester, Sex Toys, Sounding, Spanking, Voyeurism, Watersports, don't read if you don't like non-con, i guess?? but there is no one watching just sexy stuff in a public place, if diuretics counts as drugs, sam tricks dean into wearing a cock cage and a sound, very non-consensual, wow there's actually a tag for that
Language: English
Status: In-Progress
Published: 2017-10-03
Updated: 2018-03-12
Packaged: 2019-01-08 17:20:47
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 8
Words: 24,378
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12258726
Author URL: https://archiveofourown.org/users/NinNinNin/pseuds/NinNinNin
Summary: Dean gets hit with a curse that make him hard and leaking cum constantly. Sam's brilliant solution? Put Dean in a cock and sound cage.OrThe one when Sam fulfill his dirtiest fantasies about his brother





	1. My Brother's Key Keeper

**Author's Note:**

> So this is by faaaar the most Explicit story I have written so far. But I've been reading a lot of similar fanfic in the spn fandom and i felt I wanted to add my own to it! So here we go, the first chapter of hopefully many more :3 Please enjoy purgatory with me ~~
> 
> Also,  
> I don't have a beta, but if anyone is up for it, I'd love for someone to help me improve this story by betaing it!  
> UPDATE: I now have a beta reader!!! The very kind and talented SanuraKitKat is now helping me out! <3

Sam couldn’t believe how lucky he was that he got to play out one of his darker, dirtier sex fantasies with his brother. He should really sent a gift basket to that witch. If, of course, he manage to find her before Dean killed her.

“Are you sure there is no other way?” Dean groaned as Sam pressed the ice pack that was wrapped in a towel on Dean’s cock firmer.

“Well you basically got one more option and that is to stay in here and be well hydrated so you don’t run out of fluids until I find the witch.”

“No way in hell, that witch is mine.” Dean growled, his hands clutched around the sheets as the coldness forced his cock to slack temporarily.

The witch that they had tracked down had manage to escape, but not before placing a curse on Dean, a curse that made him hard and dripping precum constantly. It was one of those ridiculous curses that only really bad porn movies would have, but still, that was the one the witch had used. They had manage to figure out that it wasn’t a permanent one, if they killed the witch the spell would break. The spell that forced Dean to get hard even when he didn't feel like it or even had any come left and also made him flow a constant stream of precum, even after he had orgasmed. This Dean had found out the hard way.

So after a few hours of Dean jacking off and Sam researching, the current plan had slowly emerged in Sam’s mind, about how a cock cage could prevent Dean from getting hard and how a urethra sound inside his cock would stop the precum from leaking, effectively blocking off the stream. Sam had managed to convince Dean that this was the most effective solution, mostly thanks to his convincing tone and Dean’s not so clear mind.

“Okay so.” Sam held up the cock cage, careful to not let his excitement show. “You ready to be locked up?”

“Don’t say it like that.” Dean groaned and closed his eyes. “Just get it over with.”

That was all the approval Sam needed before he placed down the ice pack and slipped the cock cage on. The cage had a nice ring that fitted snugly behind Dean’s balls, and the nice smooth plastic looked stunningly good around Dean’s cock, a big lock on the upper side perfectly to make sure Dean didn’t try to take it off himself. Sam had chosen one that was average, loving how his brother’s cock looked filling it up, the cock already trying to get hard inside the cage, but not succeeding. Sam had to shift so his half-hard cock wouldn’t be so visible, not wanting to ruin the moment by having to explain to Dean why he found locking him in made Sam so aroused. Especially not since he still got to plug his brother up.

“Oh fuck, I’m gonna kill that bitch so slowly,” Dean hissed as his cock tried to get hard.

“I’m not gonna stop you.” Sam replied, carefully swabbing the head of Dean’s cock. “I’m gonna insert the rod now.”

“Okay.” Dean swallowed hard, trying to maintain his composure.

“You may feel some slight discomfort at first.” Sam said before starting to push in, swallowing hard as Dean’s cock hungrily took it all in. Sam might have gone easy on Dean with the cage, but the sounding had always been a special kink for him and he really didn’t want to waste such a golden opportunity. He had gone with one of his own personal favourites, one with slight bumps along the way, bumps that got bigger near the end. It wasn’t the longest one he had, but it certainly wasn’t the smallest. Sam knew Dean would be feeling every bump as it slid inside of him, and he could see that the process of it going in made Dean shiver and his own cock twitch with arousal.

“Oh fuck, Sammy.” Dean involuntarily moaned, one of his hands flying up to cover his mouth. “Is it supposed to be this long?”

“I’m sorry Dean, this was the only one they had at the store.” _Lies._ “I’m so sorry, but this is the only way.” _More lies._ Sam was not going to let Dean know the truth, about how he had found a spell that would have ended Dean’s distress in just a few seconds. Oh no freaking way.

Sam loved how Dean’s urethra slowly stretched around the sound, getting wider as the rod became bigger, until it reached the end, where a hole was, perfectly lined up with two holes on the end of the plastic cage, so that one could put a lock through all three holes it to prevent the wearer to take it off themselves. Which was exactly was Sam was doing.

“And as we discussed, I’ll be keeping these two keys.” Sam said as he placed the two keys on his key ring, one for the cock cage and one for the sound. Of course he also had spare keys in his duffle bag, but he wasn’t going to let Dean know about it, unless an emergency happened.

“How did we reach that conclusion again?” Dean asked as he looked down on his thoroughly caged cock, a pained expression plastered on his face.

“Because we do not know exactly how the curse will affect your rational thinking and we do not want you to forcefully rip it out and damage your urethra.” Sam explained calmly, patting himself on the shoulder for coming up with such a perfect excuse for being the key master.   
“Now, how are you feeling?”

“Like someone has rammed my cock with a tree and squeezed it between two very big rocks.” Dean said as he gingerly stood up and Sam swiftly got up from the floor before turning around, heading toward the bathroom in order to hide his hard-on.

“Perfectly peachy then. I’ll give you some, um, adjustment time.” He barely made time to lock the door before he yanking his pants down, furiously stroking his cock before spilling his cum into the toilet.

_“Man, this is gonna be great.”_ Sam could finally allow the smile to cross his face as he imagined how thrilling the following days would be.


	2. A Golden Morning Time

**Summary for the Chapter:**

> Sam helps Dean with a predicament in his morning routines.

**Notes for the Chapter:**

> Thank you so much for all the kudos and the lovely comment by Fundle (I hope you’ll enjoy the bs level in this chapter). Please enjoy this chapter that includes much bullshit and much pee talk. And new depths of torture for Dean, much to the joy of Sam. This story is really a slow burn so I’m sorry, but you won’t get to read Sam fucking Dean for a few more chapter. But don’t worry, it’s getting there ;)  
> .  
> .  
> .  
> Includes lies, alcohol and catheter, but not exactly in that order. As before, please join me in purgatory in this very unbeta second chapter.  
> EDIT: This chapter has been beta'd by the awesome SanuraKitKat!

The following night in the shady motel room was restless for both of them. Dean slept fitfully, the curse messing him up even when he had knocked back a whole bottle of whisky, not letting him escape entirely from the lust that coursed through his vein, making him desperate to jack off even when he was exhausted and drunk as hell. The confinement of the cock cage wasn’t helping either and Dean kept waking up to find himself rutting his caged cock on the bed or the pillow, his clothes damp from the sweat he kept producing in his frustrated state.

Sam wasn’t much better. The tiny gasps and muffled groans that Dean was making in his fitful state was driving him crazy. At the beginning of the night it had been a treat for Sam, as he royally enjoyed jacking off to Dean’s distressed noises in his own bed, picturing just how sinfully disheveled his brother would sound later if he was already making such cute moans after just being locked up a few hours. Then, after two orgasms, when Sam had lulled to sleep, he had been pissed to wake up to Dean thrashing around in his bed, cursing loudly in a slurred voice. And since Sam had already taken care of himself already, he wasn’t up to playing with himself one more round, no matter how cute his brother sounded. Now it would be another thing if the real deal would wrap those rough hands and plump lips around his cock but… all good things comes to those who wait. And Sam had a five-step program.

So instead Sam settled for at least trying to sleep, knowing nothing would come from trying to soothe Dean when he was in that drunk state, especially since he had no plans of helping Dean come anytime soon. Beside, that wouldn’t solve the problem at all and it most certainly wouldn’t help him get Dean whimpering and shivering and begging to take his cock...Sam smiled as he kept on picturing all the dirty scenarios he had planned for the following days. But none of that would happen if he was hasty. So he slept, fitfully, trying to block out Dean’s   
groans from the bed next to him.

Eventually, morning came with neither of the Winchesters in a refreshed and well-rested state. However Sam was giddy with excitement over what the morning routines included; releasing Dean momentarily from the sound so he could pee.

“Good morning, Dean, did you sleep good? At all?” Sam tried to keep away his glee from his voice, but apparently a bit slipped out, if Dean’s stink eye was any indication.

“I have slept better in a fucking haunted chainsaw factory! Hell, I’m even thinking about chopping my dick off and having Cas heal me just to see if it will reset this fucking curse.”  
“I’m pretty sure that’s not a good idea, Dean.” Sam smiled, masking his indignation about hearing his brother talking about that damned angel with fake sympathy. “But hey, I’m gonna help you take off the sound for a bit so maybe that will give you some relief?”

“Yeah maybe.” Dean groaned as he got up from the bed and headed toward the bathroom, Sam following him close behind. “Hell, I might feel a bit better after taking a good piss, right?”

Sam quickly unlocked the sound from Dean’s cock, trying to not show how he enjoyed the downright illegal noises his brother made as he slid the rod out, making sure every bump rasped against Dean’s slit on the way out. Then he quickly excused himself and left Dean alone to pee in peace as he cleaned the rod, not wanting to ruin any of the fun he had planned with any infections.

Sam almost dropped the rod in surprise as he suddenly heard Dean swear loudly and banging on the door with both his fists and legs by the sound of it.

“Dean? What’s the problem?” Sam slowly inched towards the desk, where they had left their guns the evening before. “Dean?”

Sam managed to go through at least three different scenarios of Dean laying strangled, beheaded, or bleeding in his head before Dean answered him in a strangled, uncharacteristic choking voice.

“I can’t, fuck, Sammy, I can’t--It’s not-- fuck, it’s not coming out.”

“Oh.” Sam felt a smile creep up on his face and he felt how a rush of arousal swept over him as he realized what Dean meant. _“Oh, this is great. This is like ten Christmas’ all at once.”_  
Sam cleared his throat and tried to calm himself as he leaned against the bathroom door.   
“It’s okay Dean, it’s just a side-effect of the spell, okay? Hey, let me help you with it.”

There was a silence that seemed to go on forever until Sam heard Dean shuffle around on the other side and he exhaled a breath he didn’t even know he was holding in as Dean opened the door.

The scene that met him was simply breathtaking, his usual proud brother was eyeing him with pleading eyes, one of his hand clutching the hem of his t-shirt like he was five and hiding his pee-pee. Sam wished he could snap a picture of this, but no time like the present he guessed.

“Dean, it’s okay, it’s just me. You trust me, right?” Sam cooed, putting on a disarming smile and holding up his hand.

Dean licked his lips, his gaze wavering somewhere over Sam’s shoulder before settling on a spot somewhere around Sam’s left ear.

“Yeah.” That was all the approval Sam needed.

“Okay, hang on, I’m gonna go get something from my bag. Don’t worry, it will just take a sec.” Sam hurried to turn around and almost dash to his bag before Dean could change his mind. Sam hadn’t really believed he would ever get to use that item, but it seemed like he really was being blessed by some Goddess right now. Sam quickly snatched the small bag he had kept in one hidden pocket in his duffel bag and quickly got back to the bathroom, when Dean was still standing, slightly crouched with his pants still on the floor and his hands nervously fingering the hem on his shirt. Sinfully adorable.

“Okay, I need you to sit down on the toilet for me and spread your legs.” Sam instructed his brother.

Dean hesitated for a moment, but then his desperate need to pee won over his embarrassment and he slowly sat down on the toilet.

“Now please hold up your shirt for me” Sam instructed, enjoying himself tremendously over having the upper hand. He unzipped the bag and took out a small bottle of lube and some cotton swabs with cleansing solution already on them.

Dean carefully followed every move Sam was making, his forehead covered in sweat and his hands still clutching the hem of his shirt, still covering himself up much to Sam’s dismay. _“Gotta have to train that hesitation right out of him.”_

“Is that,” Dean licked his lips, swallowing roughly, “is that what I think it is?”

“It’s a Foley catheter yes. It’s used frequently in hospital for patients with urine-related difficulties.” Sam explained smoothly, placing a warm hand over Dean’s knee, looking him straight in the eyes. “You don’t have to worry, Dean, I know exactly what I’m doing. Jess showed me.”

“How-” Sam cut Dean off, not in the mood to try to lie his way out of this one, too eager to get to the next phase.

“Dean, does it really matter? Shouldn’t we focus on your problem right now instead? Or do you want to keep being in that state?”

Sam’s question seemed to bring Dean back to his problem at hands. Dean grimaced and shook his head slightly, wincing as he shifted slightly, clearly feeling the pressure of his pent-up cock in more ways than one.

“Yeah, just--, fuck, Sam-- is it gonna hurt?”

_“No, but it’s not gonna be a good experience. For you at least.”_ No, it’s just gonna be a bit, uh, uncomfortable for you, especially with your bladder that full. And also, thanks to your, other predicament.” Sam didn’t have to specify what other predicament, Sam could clearly see the small puddle of precum Dean had left on the floor where he had stood earlier.

“Yeah, okay.” Dean finally lifted the hem of the shirt up for Sam. “Let’s just get this over with.”

_“Oh, I’m gonna savor this.”_ “I got you, Dean. Don’t worry.” Sam promised as he crouched down, popping the cap open to the lube to smear a small amount on the tip of Dean’s cock. Sam was extremely grateful that Dean wasn’t questioning his rather extreme methods in this matter, because he was running out of bullshit answers pretty fast. He was pretty sure he had the mix of a massive hangover, sleep deprivation, and a wicked curse to thank for that.  
“This will probably feel pretty odd, but try to relax.” Sam warned after he had quickly cleaned the catheter and position himself so he could hold Dean’s cock in one hand and the catheter in the other. “I promise it will be worth it.” Sam had to take some deep breaths to not give away his arousal and keep his hands steady.

Dean only gave a small whine as response, clearly doing his best to act tough with the remains of his dignity. Sam was going to love stripping every last scrap of that away.

“Alright, here we go.” Sam steadied his hands and slowly started inserting the catheter, inch by inch, all accompanied by small choking noises and swear words from Dean. When Sam was certain it was deep enough he gently inflated the small balloon that was at the end of the catheter in Dean’s bladder, to make sure the catheter would stay inside Dean as long as he wanted it to be there. Then he gently probed the catheter along until he was certain the balloon nestled at the bladder’s neck.

“Okay, Dean, I’m gonna unclip the tube now.” Sam said, hoping Dean wouldn’t notice the waver in his voice.

Dean only hummed, his gaze steadily fixed on a spot above Sam’s head, his chest heaving in short, rapid bursts.

Sam kept his eyes on Dean’s face as he slowly took off the clip, finally allowing Dean to get some release.

The effect wasn’t instant, but as the pee kept flowing out of Dean in a steady stream, Sam could see how Dean relaxed and an expression of pure relief settled over his face, wiping out the frown Dean had had ever since they had encountered the witch.

“How does it feel, Dean?” Sam had to dig his nails into his arms to not whip out his cock right there and then and just spurt all over Dean’s stuffed and abused cock.

“It’s--oh fuck, Sammy--I can’t-- I can’t describe it.” Dean groaned, his eyes glazed over as he leaned back to let the toilet support him, giving Sam an ever better view. A steady yellow flow was still filling the catheter tube, passing through Dean’s slit, which was slightly red, making a gorgeous contrast to the plastic cage around it, the cock inside it still making a remarkable job of filling it out to the brim. It was obvious the curse was still very much in effect. Dean’s balls were still not as full as Sam was hoping they would be, but still looking soft and just begging for a good spanking session. Sam made a special memo to get to that later at some point. He also made a note to buy some ball stretchers and weights on his next shopping spree.

“Hey Sammy.” Sam looked up abruptly, hoping his brother wasn’t going to call him out over staring at Dean’s cock in a very unbrotherly way.

“Yeah, Dean?”

Dean dragged a hand over his face, grimacing over the amount of sweat he had produced before clearing his throat. “I just--man, this is such a fucked up situation. And we’ve been in quite a few fucked up situations, haven’t we Sammy?”

Sam exhaled sharply, before giving Dean one of his best ™ lil shit smiles. “Speak for yourself.”

“Bitch.”

“Jerk.”

“Hey, Sammy,” Dean finally looked at his brother. “Thanks for having my back.”

If Sam was a better person, this show of affection and trust would probably have made him instantly undo the spell and end his brother’s suffering. Unfortunately for Dean, Sam had passed that level of goodness many, many years ago.

“Yeah, Dean, of course.” Sam smiled, already thinking how much fun it was going to have Dean plugged up and miserable the whole bumpy car ride to Nebraska on a wild goose chase for a witch who had never sat her foot in that state. “That’s what family is for.”

**Notes for the Chapter:**

> I need to clear my history browser after writing this chapter...
> 
> Please leave kudos or comments if you'd like me to continue this story!


	3. Some Fun On the Road

**Notes for the Chapter:**

> Chapter 3 Who says the fun has to start when we get there and not on the road?
> 
> A/N: I basically wrote five pages of this chapter, then scrapped half of them cause I felt the story was going down the wrong road (gonna include that part later on instead), so this took a bit longer to write than I had originally planned. Anyway, here we go, the next part on this choo-choo sin train. Please enjoy on your own risk! Beta'd by the incredible SanuraKitKat! 
> 
> Also huge thank you to Fundle and then there was someone else who wrote some incredible comments in their Bookmark sections (thought I can’t find that now, hmm….), you really gave me some great ideas and also including everyone else who left comments and kudos, this chapter is to all of you!

The morning sounding session had been the best way to start a day if you asked Sam. Of course, Sam would have enjoyed it even more if he would have woken up with Dean deep-throating his cock, wearing nothing but a thick sound and a butt plug fitted with a tiger tail. San could picture how Dean’s lips would look around his cock, all read and plump, strained, the hair around his cock tickling Dean’s nose, the small choking noise Dean would try to hold back, knowing the amount of spanking he would earn if Sam heard them…

“Hey, earth to Sammy? What happened to the coffee?” Dean’s voice snapped Sam back to reality and Sam hurried to pour the coffee in the cup before offering it to his brother, who now looked if not fine, a little less flustered and kept together after he had taken a quick shower and gotten into some of his regular clothes. Jeans and a clean striped shirt, this one in a nice green color that really brought out the green in Dean’s eyes. Of course, Sam had a feeling Dean would look even better in a spiked collar and a two size too small cheerleader outfit but… Fuck. he really needed to cool off. If things progressed like this, he would jizz his pants faster than Dean and that was most certainly not the plan.

After Dean had peed, Sam had smoothly removed the catheter from inside Dean’s cock and inserted the previous sound. Dean hadn’t even protested, only made a slight whining sound in the back of his throat, making Sam feel proud over how Dean had seemed to accept his situation and the shift in command. Sure it would have been fun to leave the catheter inside Dean, but Sam liked sounds more, and beside, the sounds he had were bigger that the catheters and also a more versatile tool, meaning it would be more uncomfortable for Dean. And also gave him more opportunities to tease Dean and also assert his own dominance over his brother.

Sam had truly enjoyed the whole unexpected treat, but it hadn’t helped him have a clear head. The quick jack off he had managed while Dean had been in the shower hadn’t been nearly enough to quench his new thirst. But now he had to be even more careful not to show his real feelings, now that he was so close to actually being able to pull of his dark fantasy. Dean might be dulled by the spell and all the side effects that came with it, but Sam knew he wasn’t stupid. If he didn’t play his cards right he would suddenly lose his upper hand.  
And that was the reason Sam had rushed through his jack off session in order to be able to start preparing the morning coffee and the diuretic he had stolen from a hospital they had visited a few weeks earlier on a case. It had been child’s play for Sam to pour a generous amount of diuretics into the coffee while Dean changed clothes.

Sam knew of quite a few ways to make a road trip more exciting and this was one of his favourite ones. And this time he got to add in another one of his favourite sex situations, the one with Dean pleading and begging him to pee. Sam had to turn away and pretend to check his bag for something so Dean wouldn’t see the wicked smile that flashed across his face and the slight bulge in his pants.

Sam cleared his throat as he zipped his bag shut. “So, are you ready to hit the road? You feel good enough?”

“Yeah, the faster I can get to that witch, the better.” Dean made quick work of his sandwich before crunching the paper cup the coffee had come in and throwing it in the trash can.

Sam observed his brother as Dean gathered the few belongings that was still spread out in the motel room they had shared. Someone who didn’t know Dean would probably not even notice anything out of the ordinary, except maybe that Dean was walking slightly odd, like he had a slight limp or something. Sam, however, who was well familiar with Dean’s antics and tell tale sign, could see the flush on Dean’s cheek, the unusual absentmindedness he showed when packing his bags, and how his hands was slightly unsteady as he checked his gun. _“Oh yeah, Dean might be looking fine, but there is probably only one thing on his mind that won’t leave him alone.”_ Sam licked his lips and snatched the car keys from the table.

“Hey, what do you think you’re doing?” Dean protested loudly as he saw what Sam was thinking.  
“Dean, do you really want to drive in your state of mind? Do you really want to risk crashing your precious baby while keeping your hands off your junk?” Sam questioned, knowing he had hit the right buttons by the way Dean made an ugly face.

“Fine, fine. But if I for even a sec think-”

“Yeah, yeah, let’s just load the car and get going? If we’re lucky we’ll get to Nebraska before nightfall.” That made Dean hurry and soon the brothers were out of the road again.

It took roughly half an hour before the diuretics kicked in and Dean started squirming in his seat. And half an hour more before Dean had enough.

“Sam, stop the car.” Dean said one hour later after they had headed off from the motel, his left leg jumping restlessly up and down like it was on an invisible string.

“Dean, we only started an hour ago, you can’t possible have to pee so soon.” Sam huffed, masking his joy over that the diuretics was clearly doing it’s job by appearing to be annoyed by Dean’s request. “If we have to stop all the time we won’t be able to make it to Nebraska before the sun sets.

“Yeah, yeah, I know, I know, don’t get your panties in a bunch.” Dean straighten up and spread his legs as wide as he possible could in the cramped front seat. “Just try not to drive in any holes okay?”

Sam gritted his teeth but kept up his little brother act. “Of course, Dean.” He knew it wouldn’t be long before Dean was going to break.

Three songs later he was proven right.

“Sammy, pull over, seriously, I really have to take a leak.” Dean had been squirming in his seat all the way through the last guitar solo on the radio and and Sam had to give him credit for not snapping already and just pulling on the steering wheel by now and forcing the car to a stop.

“Dean, you know you don’t, it’s just the curse making you feel like you need to go, pushing on your bladder. _” Or the diuretics doing it’s job._ “Just hang in there okay?”

“I can’t. Sammy, you have no idea-- it’s not--” Sam could hear the frustration in Dean’s voice, how Dean’s carefully carved poker face was falling. Sam stole a quick glance from the road to look at Dean’s face and felt a jolt of pure glee as he saw that the flush of uncomfortable and awkwardness mixed with arousal was back on Dean’s face again. Clearly the diuretics was doing it’s job of making Dean feel like he needed to pee and the boost of the curse was doing it job to double that effect. But Sam felt that Dean wasn’t really ready for the next step yet so he simply gave Dean’s knee a quick squeeze while keeping his eyes on the road.  
“Dean, it’s okay, I get it. But we can’t keep on stopping, you know that right?” Sam said in a reassuring and authoritative voice. “you won’t feel any better if we did. Think about it logically, you haven’t drunk enough today to need to pee again, right?”

Dean made a low whining noise that made Sam discreetly adjust his pants.  
“Fuck, Sammy, I know you’re right, but-- fuck can you just stop? Please?”

Oh, Sam loved to hear Dean plead but Dean wasn’t even nearly near the point of breaking that Sam wanted him to be before he moved on to the next part.

“No. Dean, you are not thinking straight and I’m the one driving so I decide when we stop.”

“Sammy, could you -”

“Dean, I’m gonna give you two choices. Either you keep your mouth shut for the next hour or I throw the keys to your manly parts out of the window and you have to be like that until we find a hardware store, which will likely not be until we reach the next city in two hours.” Sam cut Dean off in his most no bullshit voice, which he had never talked with when Dean had been present. Sam could feel Dean’s eyes on him and he had had to use every ounce of his willpower not to turn to Dean to see the look on his face. Sam really hoped Dean would go along with the first options, since he didn’t really wanna go through the second one, not knowing if he could pull off listening to Dean whine and moan for two hours without jizzing in his pants like a teenager.

The moment stretched on for what seemed like forever for Sam when he feared he had gambled to high and Dean would call his bluff, before Dean clicked his tongue and punched the radio, switching from the radio to the cassette player, filling the car with heavy bass and drum solos as Dean rolled his seat backwards, settling into his seat with arms crossed and legs jumping up and down.

Sam had to bite the inside of his cheek to not laugh out loud in joy.

See, Sam had always sensed that Dean hadn’t really been the swaggering, confident alpha male he seemed to make everyone believe he was. Sam had seen the way Dean had acted around their father, the way his back had straighten every time their father had arrived, the smooth transition from one position to another Dean had went to every time John Winchester barked an order on a hunter job that Dean had pulled off.

And Sam should know, heck, he had practically watched Dean like a hawk ever since he was old enough to focus on anything else than his own fingertips. Sam had been looked up to Dean ever since he was four and he had been there to see the change in Dean that had happen when their father had left them alone, the strain in Dean’s eyes as Dean had tried to pull off being the big brother their father had ordered him to be. He had been there when John had lashed out on Dean for leaving his baby brother alone and sneaked off with some dumb blonde with more bubblegum in their head than in their mouths and later on, when he had started to realize his feeling for his brother might not be purely brotherly, he had wondered if it hadn’t been Dean’s way of trying to get their father’s attention, Dean’s struggle to get back to the ways things were, before he had to be the alpha male and not the submissive bitch he clearly was meant to be?

Sam had always had an odd sense of guilt when he had seen Dean declined offers of hanging out with chicks or party invites in favour of hanging out with Sam instead, but he had always been overjoyed when Dean did it, which had also made the guilt double back inside of him. And then, when he had turned old enough to be left old enough and clever enough to find his way around different websites, Sam had started to figure out that his...sexual urges might not exactly be what was the norm. Especially not the urges he felt towards his own brother. Sam had been terrified the first time he had stumbled upon his first S/M porn video, the shame and arousal that washed over him so overwhelming he had almost been unable to clear his history browser after he had jacked off. Of course, he hadn’t stopped there and many many videos later, it had lead him to this moment, which he was enjoying royally.  
Sam had to give Dean credit, he hadn’t really thought Dean would be able to go one more hour without talking and pleading, but as usual, his brother went over and beyond his expectations. One hour passed with no more talk from Dean, just some slight vocal noises from him.

“Good job, Dean. I’m so proud of you for keeping it together for one hour.” Sam finally turned over to Dean after one hour had passed, giving him a small smile. “How are you feeling?”

“I’m--,” Dean licked his dry lips, his cheeks flushed and his voice unsteady. “I really need to pee, Sammy.” He kept his bent forward position, his hands pressing against his crotch as he had been doing for the last thirty minutes, like he was afraid to move in fear that he would leak. Which was adorable, considering that it was impossible for him. Sam felt his heart swell over how great Dean had followed his orders and obeyed him even when he had clearly wanted to pee for the last one and half hour. _“Looks like Dean truly is a pure-blood bitch.”_ He suddenly thought of a great idea to take Dean’s obedience training one step further. This was the perfect opportunity to teach Dean the reward and punishment system.

“I know you do Dean, but you’re doing so great. It’s only one more hour now until some civilization, so let’s keep going and stop at a restaurant, okay? I know you can do it.” Sam soothed, delighted by the horrified noises his suggestion made Dean make.

“One more fucking hour?? Fuck that, Sammy, there’s no way I can do that!” Dean protested vehemently. “Sam, stop the car right now! That was the fucking deal!”

“Dean, swearing and yelling ain’t going to solve anything. Also, I don’t remember ever promising anything about actually stopping, I just say that if you weren’t quiet for the next hours I would throw out the keys, remember? And I kept that promise.” Sam switched to his more authoritative voice. “And I could still throw out the keys if you don’t behave. Or even refuse to let you pee until we get to the motel.”

There was a moment of silence when Dean inhaled sharply and squirmed in his seat, probably being horrified by the mere thought.  
“That’s fucking five hours from now! You wouldn’t!” Dean’s voice was trembling slightly and Sam had to mask his glee with a scowl.

“Dean, what did I say about swearing? I really don’t think you should be making me angry right now. Also, we’ve been drinking the same amount of liquid today, I really don’t understand why you’d have to take a leak again. Or do you really like having my hands on your pee-pee that much?” Sam was happy to only get a discoherent spluttering as an answer to that. Sam glanced over and saw that the flush on Dean’s face was back at full power. _“Good, looks like the curse is also back in full power. That comment probably made Dean even more focused on his dick.”_

There was another pause there, with only the the music filling the space between them, before Sam decided to play his next card.

“You know Dean. I’ll make you a deal. I’ll let you pee if-- nah, forget it, you’d probably never do it.” Sam waved his hand, trying his best to look embarrassed.

“Do what?” Like Sam had hoped, Dean was quick to take the bait. “Don’t play cheeky with me, Sammy.”

“Well, you see, you know I, um, I haven’t really had any luck with girls lately right? So I’ve been--, well to be honest, I’ve been pretty pent up lately and this whole,” Sam gestured vaguely towards his brother, “this whole witch deal hasn’t really left me with much me time.”

“What are you getting at?” Dean said with a frown, clearly not seeing where this was. Sam couldn’t really blame him, since this whole story was so fake you could basically pull a rabbit out of it.

“I guess what I’m saying is that, if you lend me a hand I’d lend you mine.” Sam answered, seeing how the realization of what Sam wanted sinked in for Dean.

“You want me to-- jack you off?? That’s-- fuck-- Sammy, that’s disgusting!” Dean swore, leaning heavily on the doorframe, trying to get further away from Sam.  
“Well, you just upped the offer into you sucking me off for me to let you pee, but yes. And I never said you had to do it.” Sam shrugged, like he didn’t have a care in the world what Dean chose. “I’m just saying, an eye for an eye kind of deal. Take it or leave it. Hey, since I’m a nice guy, how about you even get a reward? If I think you’re doing a good job, I’ll even let you take a shower completely unlocked and cage-free.”

Sam switched the radio on to let Dean ponder about the offer and a news reporter filled the car with her talk about boring news like some politician taking bribes. Sam knew this was a gamble, but he also knew Dean must be feeling pretty excruciating with the diuretics making him want to pee so badly it would even be a physical pain and then the curse making him want to ejaculate. The tantalizing promise of being out of the cage was probably also a pretty good carrot for Dean.

It took roughly five minutes for Dean to break.

“You promise you’ll let me pee if I do it?” Dean said in such a low voice Sam wasn’t sure he even heard right.

“Yes, Dean, as soon as you’ve made me cum I’ll take out your sound.” Later on, Sam was going add in some longer endurance training, but right now, he was really proud of Dean for going this long with the sound in. Especially with the added effect of diuretics. And Sam was even more happy about how obedient Dean was behaving. He felt giddy with how fast Dean’s bossy and dominant side was crumbling, leaving his much more appealing slutty and submissive side emerging.

“Okay. I’ll do it. But you better not tell anyone about this.” Dean warned, a sharp glare in his eyes that even dulled the otherwise adorable flush he had going on.

“Wouldn’t dream about it, Dean.” Sam smiled as he pulled over, finding the perfect forest road for some privacy. _“This will be just our little secret, my baby brother.”_

Sam unbuckled his seatbelt and spread his legs even further apart to give Dean better access in the cramped space. Sam really loved how this day was turning out to be.

“We’re doing it here? In the car?” Dean questioned, his fingers shaking trembling as he unfastened his own seatbelt, his gaze flickering between Sam’s crotch and a point on Sam’s shoulder.

“What? You’d rather do it outside when anyone could see it?” Sam wouldn’t mind that, heck, he could feel his cock getting harder just by the thought of Dean kneeling on the ground, his cheeks flushed with shame and his gaze flickering when he unzipped Sam’s pants, worried that someone might come by and see him..

“No, no, no, here’s fine! Let’s get this over with! I can’t fucking wait to pee!” Dean hurried to reply, maneuvering awkwardly so he was bent over the seat, his head hovering over Sam’s crotch.

“Dean, I suggest you watch your language if you don’t want me to blow off the deal.” Sam warned, putting a bit of bite behind his words, deciding he had had enough of Dean spewing of profanities like a drunk teenager trying to act cool. It didn’t fit a good, obedient boy like Dean at all.

“Yeah, yeah, I heard you the first time.” Sam could almost hear the roll of Dean’s eyes. Sam grabbed a handful of Dean’s hair and yanked hard.

“First strike.” Sam said calmly, feeling a rush of superiority by the yelp Dean gave up. “You don’t want to know what happens if you get three.”

“Yes, sir.” Dean answered in a mocking manner, but Sam decided to let it pass, hoping to encourage Dean to use that reply again, if only in a more sincere manner.

“Here, I’ll give you some help.” Sam unhooked his belt and unzipped his pants, much too eager to get to the good part to wait for Dean to stop stalling and get on with it.

“I don’t-- Fu--” Dean inhaled as Sam took out his cock, stopping the word just in time before Sam would have had to give out another strike.

“Like what you see, Dean?” Sam smirked, loving how he didn’t have to mask his emotions as Dean’s attention was all on his cock and not his face at the moment. Sam knew his cock was longer than average, and also compared to Dean’s cock slightly bigger in width.

“I’m not-- I haven’t--” Dean swallowed and Sam smiled even wider. _“This is gonna be great.”_

“Come on Dean, don’t you want to pee? And remember, if you do it well you get some shower time with just you, yourself and your pee-pee.” Sam cooed, removing his hands to give Dean more access.

“Don’t call it that.” Dean growled, but the mentioning of the reward had the effect Sam had hoped for as Dean moved his head down towards Sam’s cock without more urging.

At first, Dean was just, for a lack of better words, licking Sam like he was licking a popsicle. Sure, Sam thought it was downright adorable, his brother being this shy and cute, but it also got boring fast, as he had been horny ever since he had iced Dean’s cock yesterday. The angle and the cramped space they were in didn’t help Dean either, but Sam was sure his brother could do better than this.

“Come on, you’re not a kitty, are you? You can take me in your mouth and actually blow me can’t you?”

“Screw you, unlike you I’m not--” Dean protested, his ears red and Sam could see sweat trickling down Dean’s throat from his neck.

 _“How adorable, it’s his first time.”_ Sam mused and tangled his fingers gently into Dean’s hair.

“Okay, okay, Dean, don’t worry, I’ll help you. Just do as I say and everything will be fine, yeah? Start by opening your mouth and let the tip inside.”

Dean stilled for a moment, clearly contemplating some wise-ass remark, but seemed to decide against it, as he nodded and Sam could feel warmth of Dean’s mouth around his cock next.

“Good job, Dean. Just, slowly drag your tongue on the underside while you go down and up on me. Ju-just like that.” Sam gently kneaded Dean’s scalp under his fingers, loving how Dean’s lips felt around his cock. Dean’s moves were clumsy, the rhythm all over the place and he couldn’t even take half of Sam’s cock in his mouth. And Dean was sloppy, sometimes scraping his teeth on Sam’s cock and also spilling saliva all over Sam’s pants. Still, that hardly matter, Sam knew he was going to come soon. After all, Sam had dreamed about this for years and he had been half hard ever since the car ride started. And the noises Dean was making, the downright illegal noises Dean was making with his mouth as he tried his best to finish Sam off. Beside, as a huge bonus, Sam was enjoying himself tremendously knowing he was Dean’s first.

Sam felt how his orgasm was building up and as he felt he was just about to cum, he forcefully held Dean down to spurt in his mouth. He got an exhilarating kick hearing Dean choke and splutter and trying in vain to get away from the iron grip Sam had on him.

“What the fuck, man?? Don’t just suddenly try to choke me with your fucking cum? That’s fucking sick!” Dean lashed out as Sam finally eased up on his grip, furiously wiping his face to get all of Sam’s cum and his own saliva off.

“That’s strike two and also, no alone shower time for you. One more strike and you’ll get punished.” Sam quickly regained his posture, cleaning himself up with some tissues and making a great show of acting calm and unfazed by what had just happened, even if his own heart was still beating like crazy and his mind was playing the previous scene over and over again. “Now, do you want to keep being a lil bitch or do you want to pee?”

“Do you really have to ask?” Dean muttered, turning away to quickly unlocking the door and getting out. “You better keep your promise!”

“So impatient.” Sam sighed and slowly got out of the car, as if he had no idea about how flustered and desperate Dean was to get some release from his predicaments. Sam felt like he was high and he had to dig his nails into his palms to not giggle out loud. _“This day is just getting better and better.”_

Sam wondered how many blowjobs it would take for Dean until he could cum down Dean’s throat without him choking, having those pretty lips pressed against his balls as Dean did his best to stay still and please his brother as he swallowed obediently Sam’s thick come while suppressing his gag reflexes.

“I really can’t wait to find out.”

**Notes for the Chapter:**

> Oh boi, these chapters keep getting longer and longer ;;; I really hope that’s not a bad thing, lol. I also know next to nothing about diuretics so excuse me if this scenario is very unlikely. Please leave a comment and/or kudos if you’d like me to continue the story!


	4. A Golden Time in the Forest

**Summary for the Chapter:**

> Basically another round of watersport, now with added nipple clamps, all in the name of making Dean understand the new status quo, I hope y’all will enjoy it!

**Notes for the Chapter:**

> I can’t really express how happy I am over the positive feedback I have gotten from you all! The comments, the kudos and the subscriptions...I could never imagine that so many people that share my same kinks would like my story <3 This update is purely fueled by all the kudos and comments I have gotten! And a special thank you to Fundle, who keeps giving me more great suggestions! Thank you all for giving me the fuel to keep updating this story!  
> EDIT: This chapter is now beta'd by the awesome SanuraKitKat!

Sam observed Dean hunched over walk away from the car, making no movement of his own to join his brother. He had to admire the truly magnificent effect the diuretics were having on Dean, the way Dean was almost toppling over from the sheer effort of walking and holding it in. The way Dean was crunching his crotch between his hands, a cute flush all the way to his neck. Oh yes, Sam was definitely overjoyed by the five year old behaviour Dean was displaying with his “don’t wanna go pee-pee all over myself” behaviour. Of course, later on there was no way Sam would tolerate such a disgraceful stubborn refusal to ask for release, but right now he simple enjoyed the view. One more thing that he would enjoying teaching his little baby brother.

“Are you coming? Like today?” Dean snapped through gritted teeth as he carefully unzipped his pants as he supported his upper body on a nearby tree.

 _Make that two things to the ungrowing list._ “Of course, Dean.” Sam leisurely made his way toward Dean, fishing up the keys from his pocket as he went. Now, he had more important lessons to dish out than lecturing Dean about how to ask politely, so he simply overlooked Dean’s behaviour. For now. After all, they weren’t even anywhere close to step three on Sam’s magnificent plan.

Sam crouched down on the uneven ground, once again on eye-level with Dean’s caged cock. Deans back was against the tree and Sam was crouching right in front of him, which meant Dean didn’t really have anywhere to go and that was exactly what Sam had planned. Now, the next part of Sam’s plan was not really something he knew he would enjoy, but it was essential for his plan of shaming Dean further and a too perfect opportunity to skip in order to deal out some punishment. Sam braced himself as he started to unlock the sound.

“Okay, so Dean, just hold it in just a bit longer. Wouldn’t want you peeing all over me.” Sam said with a dry laugh, hoping Dean wouldn’t completely ruin his shirt.

“Hmp, please Sammy, it’s not like I- oh fuck!” Dean swore as his pee gushed out of his cock all over Sam’s face and hair. Dean tried to turn away, but since his back was against the tree, he just manage to press his cock closer to Sam’s face, making the pee gush more toward Sam’s shoulder and mouth. Dean froze as a wave of pure relief washed over him as he was finally being able to release himself, for the moment completely forgetting he was peeing all over his younger brother and instead let the sensation of relief wash over him, Dean’s hands firmly clutching the hem and collar on his own shirt.

Sam on the other hand, made sure to keep his mouth firmly closed and staying perfectly still until Dean’s warm pee stopped trickling down over him. Only when he could see Dean’s cock slowly starting to drip with precum instead of pee did he wipe his face with his sleeves and get up from the his awkward position on the ground to loom in front of Dean.

“Dean?” Dean clearly winced as Sam spoke.

“Dean, would you care to explain why my shirt stinks of your pee?”

“Sam, I--, fuck, Sammy, I didn’t--”

“Dean, how the fuck could you?” Oh Sam was loving this. The look of self-disgust and shame on Dean’s face. The hand movement Dean was making of wringing his shirt between his fingers. The blush that now crept all the way down to Dean’s collarbone. Oh this was worth getting peed on.

“Sammy, fuck-- I’m so fucking sorry.” Dean’s gaze was firmly planted on Sam’s shoes.

“You’re sorry? You just peed all over me and all you can say is you’re sorry?” Sam snorted, and shifted his stance, praying Dean wouldn’t notice the bulge in Sam’s pants.

“I didn’t--”

“Dean, a fucking six year old has better bladder control than you! What are you, a baby? Do you need diapers? Would you like that, baby boy? Also with all the swearing and peeing, that’s three strikes. Man, you really want some punishment don’t you.” Sam kept on, pushing all of Dean’s buttons.

“I said I was sorry? What the fuck do you want me to do??” Dean lashed out, masking his embarrassment with anger.

“Well first of all maybe, just maybe, you could show some gratitude!! Do you have any idea how hard this is for me? Do you? Do you think I actually want to have my hands on your junk all the time?” Sam really felt he should be awarded for his great acting skills.

“I-- fuck, of course I know you don’t--” To his amazement Sam saw actually tears forming in Dean’s eyes before Dean quickly swiped a sleeve over them, leaving a red mark where he swiped, much to Sam’s disappointment. _“Oh well, good things come for those who wait.”_

“Dean...” Sam felt this was the perfect moment to switch gear. “I’m sorry Dean, I didn’t mean to lash out like that.” Sam said with fake remorse as he backed a step away from Dean.

“No, Sammy, fuck, you have nothing to be sorry for! I’m the one who should--” Dean stumbled over his words, his eyes finally meeting Sam’s. The pleading and remorse that Sam saw in them made him want to just push his brother down right there and then and fuck him as hard as possible. Dean’s dripping caged cock wasn’t making it any easier either, since Dean hadn’t zipped his pants yet, much to Sam’s approval.

“Dean it’s okay.” Sam smiled reassuringly. “It’s not you, it’s the curse that makes you do all these things remember?”

“Yea-yeah!” Dean nodded, a small smile on his face. “It’s just the curse fucking everything up, right?”

 _That and then some._ “Yeah, Dean. Don’t worry.” Sam said and looked down on his shirt with a wrinkled nose. “But let’s try to not make that happen again, shall we?”

“Ah, yeah, sorry, Sammy, I promise I’ll make it up to you.” Dean laughed, scratching his head and dropping his gaze again.

That was the magical words Sam had been waiting to hear, the ones that would make this whole deal worth it.

“Well, Dean, as I said, you did get three strikes. So the best way to make it for me would be to take your punishment without any bitching.” Sam was glad Dean wasn’t watching him right now, cause there was no way he was going to keep his smile away from his face now when his plan was clicking so perfectly together.

“As long as it doesn’t involving sucking you off again, I’m game.” Dean laughed, his shoulder not as tense anymore.

“Heh, don’t worry Dean, I got something else planned.” Sam smiled back, already looking forward to when Dean would be begging to suck his dick. And no matter how much Sam would enjoy giving his brother another lesson in the fine art of pleasing him, he really wanted to try something else for now. Sam sniffed his shirt and wrinkled his nose. After a change of clothes.

“Okay, Dean, just give me a sec so I can change clothes before that, okay?”

Sam then made quick work of changing his own clothes and then scrubbing himself roughly with baby wipes to get the pees off him, or at least enough so he wouldn’t smell before they got to the motel.

Dean had been standing awkwardly beside him while he changed. The sound had easily been put back where it was now snuggly resting inside Dean’s cock again, tucked back inside Dean’s underwear. There hadn’t really been enough time for Sam to do anything more than quickly wipe the sound off and insert it again inside Dean’s coke, since Sam didn’t want to give Dean any extra time to come to his senses. Then again, Sam could tell that Dean was still very affected by the the curse, especially now when he had calmed down again and his mind wasn’t focused on the extreme need to pee. Which was great for the next part of Sam’s plan, which relied heavily on Dean’s sense of pride and remorse.

“Okay, Dean, you said you’d make it up to me right?” Sam finally addressed Dean, after getting out some items from the car in order to give Dean some new punishment.

“Yes.” Dean replied quickly, an eager expression on his face that made Sam’s heart swell.

“So, it would be fair for you to do something awkward for me now, since I just had to go through such an awkward situation right?”

“I, um, I guess?” Dean’s face scrunched up in confusion, but he was still agreeing.

“Alright. Then pull up your shirt.” Sam hadn’t actually chosen this side road by accident, it was actually a perfect spot for the thing he had planned.

“Sammy, why--” Dean closed his mouth and hesitantly pulled up his shirt, showing off his well-toned stomach, after he saw the warning glare in Sam’s eyes, probably remembering what had happened earlier when he talked back.

“Dean, it’s time for your punishment, remember? And these two are just perfect for that.” Sam explained as he opened his palm, showing Dean what he had planned for him.

“Nipple clamps?”

“Yes.” Sam was pleased he didn’t have to explain to Dean what he had planned, but he also had to push down any of his possessive and ugly expressions from his face as unwanted images of Dean trying out nipple clamps with blonde bimbos popped up in his mind. “Have you ever tried them on?”

“Nah, I had a girl who wanted to use them once but,” Dean shrugged, his eyes still on the nipple clamps in Sam’s hand. “I didn’t let her use them on me, not really into that kind of thing.”

 _“That’s what makes this so much more enjoyable.”_ Sam arranged his face again, trying not to show how much he enjoyed knowing he was going to claim another one of Dean’s “first times”.

“Well, Dean, it wouldn’t be much off a punishment if you enjoyed it right? Now, please hold up your shirt higher so I can put them on.” Sam moved forward, motioning to Dean to obey him.

“Sammy, how much will it hurt?” Dean slowly pulled off his shirt, eyes never leaving the clamps, as if he was afraid they would attack him if he looked away.

“Dean, I believe I made myself pretty clear earlier. So, either you take your punishment without bitching or you will suffer the consequences. And I promise these clamps will look like child’s play if you do.” Sam almost wished that Dean would bristle back, he had an enema mix he wouldn’t mind using. But Dean only cleared his throat and pulled his shirt all the way up, showing off his perky nipples and chiseled chest, which Sam couldn’t wait to one day pour whipped cream on and… Sam coughed, trying to gather his thoughts again.

“Okay, so first Dean, I’m going to apply this ointment on your nipples for you, it’s just to assure your skin won’t crack from the clamps, okay?” Sam smiled reassuringly, taking out a small tube, carefully making sure Dean couldn’t read the text on it. “Nod if you understand me.”

Dean looked puzzled, but he nodded slightly, pushing his chest towards Sam, making Sam wanting to hug him and coo over how adorable his baby brother was. Instead, Sam poured out a generous amount on his fingers before smearing it on Dean’s nipples, enjoying how Dean shuddered as the cold liquid touched his nipples, making them perk up to their fullness.

“That’s good, Dean. Alright, now, for your punishment. I will put these on and you’re going to wear them for two hours. If you make any sounds when I put them on, I will add one more hour. Nod if you understand.” Sam spoke slowly as he put the tube back in his pocket, making sure Dean knew exactly what the deal was.

Dean swallowed hard, but then nodded slowly, the grip on his shirt tightened as Sam lifted the first clamp to his left nipple.

The crocodile nipple clamps was one of Sam’s all time favourites. The clamps were adjustable, so Sam could decide how much he wanted his vict- partner to suffer, and also came with rings, so it was easy to add some weights to add to the pinching sensation. Sam hadn’t planned to add any weights for now, but he was keeping that as a backup plan if Dean misbehaved.

“Alright Dean, remember to keep quiet now and don’t drop your shirt.” Sam was enjoying himself tremendously, savouring the vulnerability Dean displayed and basking in how obediently Dean was taking his punishment.

Sam carefully opened the first clamps, positing Dean’s left nipple right between them and then without giving Dean anymore foreplay, firmly snapped them closed.

“Son of a-” Dean couldn’t keep himself from hissing out as his nipple was brutally pinched, but Sam had to at least give him credit for keeping his back straight and shirt up.

“That’s one more hour. It’s three now.” Sam calmly added, as he screwed the nipple a little bit more in between, enjoying the way Dean bit his adorable lips and screwed his face up, clearly trying not to make a sound. Sam knew Dean must be feeling a totally different pain that he was used to, nothing like the kind they sometimes had to pull through when fighting monsters and demons. Sam knew the pain would be subdued soon, leaving Dean with a twinge he couldn’t do anything about and sending his cock even more confused signals, heightening Dean’s already high sensitivity.

Sam didn’t give Dean any new heads up before pinching the second one on, but to his disappointment, Dean merely jumped slightly and didn’t make a sound. Sam pouted slightly as he screwed the clamps on one notch tighter before stepping back, admiring his handiwork. Sam hadn’t decided yet if he wanted Dean to get nipple rings or not. On one hand, Dean would look positively gorgeously with them, but on the other hand, like this, Sam got to enjoy trying out so many new items, and by leaving Dean’s nipple alone for awhile, the pain would be almost as high every time. _“Decisions, decision.”_ Sam smiled widely, enjoying this moment as Dean was still keeping his eyes squeezed shut.

“Alright Dean, pull down your shirt carefully, then we’re hitting the road again. We still have a long way before we reach Nebraska.” Sam eventually said, keeping his glee over the continued car road carefully to himself. _“This will so be worth getting pissed on.”_ Sam couldn’t wait to dish out the next punishment and he was confident he wouldn’t have to wait long. Oh he was certain he wouldn't have to wait long.

**Notes for the Chapter:**

> Please leave kudos and comments if you’d like me to update this story! ^^ Also, please comment if you think there is any tag(/s) I should add!


	5. An Itch I Can't Seem To Scratch

**Notes for the Chapter:**

> A/N: I will never apologize for bad titles, but I will apologize for all the typos I make, like yikes, I’m so sorry ;;; Thank you all for continuing reading this even when I make so many errors. With that said, this fic now has over 200 kudos. Like. Wow. I get a kick every single time I think about it. Thank you, thank you so much! Every update is for every single one of you who left kudos and commented and subscribed to this story. Here’s another one for the road for all of you. Let’s keep sinning together ;)
> 
> EDIT: This chapter is now beta'd by the truly amazing SanuraKitKat!

Sam made sure Dean didn’t try to remove the clamps when he put his shirt back, even going as far as pinch them slightly to make sure Dean was still feeling them, loving the moan Dean unsuccessfully tried to cover up with a cough. 

“Alright Dean, time to head back on the road.” Sam motioned to Dean to get in the car. “Oh yeah, one more thing before I get in.” 

“What is it?” Dean had gotten his frown back, but Sam was pleased that he made no move to get up from his seat even as he saw what Sam had taken out from the trunk. “Oh no, Sammy, you got to be kidding me.”

“No, Dean, this is the last part of your punishment, please place your hands behind the seat.” Sam clanked the handcuffs around in his palm. 

“That wasn’t in the deal!” Dean protested, childishly crossing his arms in front of him, but then yelped in pain and quickly uncrossed them, as he remembered his clamped nipples. 

“I never said that.” Sam opened the back door, crawling inside slightly so he could handcuff Dean. “Dean, I can’t make sure that you don’t touch your nipples while I drive, so I need to cuff you. Or do you want me to drive unsafely?”

“How about you just keep your fucking eyes on the road and trust me?” Dean snapped back, making Sam feel the blood pump in his ear faster and he had to inhale sharply to not slap Dean. Instead he grabbed a handful of Dean’s hair harshly, yanking it hard and pressing his face close to Dean’s ear.

“Don’t test me, Dean.” Sam said in a low voice, so close to Dean that he could hear Dean swallow. “I’m going to punish you for that remark later, but right now, I want you to put your arms behind you. Now.”

Sam almost wanted Dean to challenge him again, feeling a great rush from being allowed to reprehend Dean like this. He could think of at least ten different ways to make Dean feel sorry for talking back. Though that would speed thing along a tid bit faster than he had planned, but Sam didn’t mind sacrificing that, as long as it made him come out as the winner in the long run. But he would much rather play the longer game, so he decided to try one more time to get Dean to go along willingly.

“Dean?” Sam dug his nails harder into Dean’s scalp, enjoying the shudder that ran through his brother. “Remember that promise of making it up to me? Or, would you prefer an eye for an eye kind of deal instead?”

“N-no.”

“What was that? Louder, please.”

“I said no.” Dean cleared his throat and slowly stretched his arms behind him. “This works.”

“That’s better.” Sam released his grip on Dean’s head and snapped the handcuffs on Dean’s wrist with a satisfactory snap, making sure they were tight, but not so they stopped the blood from circulating.

Sam made sure to compose himself as he closed the back door and went back to the driver’s seat, getting back to act like the goofy brother who just meant well.

“Alright, Dean, sorry about that, I just,” Sam laughed, trying to sound embarrassed, “still a bit riled up over getting peed on I guess.” 

“Don’t sweat it. I mean, if this is all it takes to get back on your good side then I’m all in.” Dean replied back as a bit of the tension left his face, as he tried to find a good position with his arms, cock and nipples in a compromised state. 

“Good, good, now Dean, no nagging or bitchin, okay? It’s only one more hour until we reach the next city, then we’re getting some food. I’ll even let you choose the food if you’re good.”

“Sweet! We’re getting hamburgers then!” Dean perked up, the promise of some greasy meat all it took to bring a smile on his face, despite the situation he was in. Well, Sam guessed, with the kind of life they had, every silver lining was worth cheering for. 

However, it didn’t take long for Dean to start squirming in his seat, much to Sam’s satisfaction.

“Sammy, please uncuff me, my nipples aren’t feeling so peachy.”

“Haha, nice try Dean. You ain’t getting out of them anytime soon.” Sam rolled his eyes in good humour, his gaze fixed on the road.

“Please, Sam, please, just-- please check my nipples at least? This itching is driving me crazy!” Dean pleaded, clearly not in a good place.

Sam had to bit the inside of his inner cheek to not smile wickedly. _“Oh I bet it does.”_ The itching lotion was working wonders. He had bought it long ago at a prank store, thinking it could come in handy someday. And now Sam gave himself a mental pat on the shoulder for coming up with that particular bright idea to spice up this second part of the road trip even more. Of course, he was training Dean to be an obedient little bitch, but right now, he was far more enjoying dishing out punishment...

“Dean, just hang in there okay? It’s just because you aren’t used to the feeling of nipple clamps, that’s all.” Sam explained, tapping lightly on the steering wheel. “Just, sit still and listen to the music instead.”

Dean huffed, but fell silent for a while after that and Sam could see how Dean was doing his best to sit still, but he was still pouting in a very adorable childish way.

Now, if Sam hadn’t smeared the itching lotion on Dean’s nipple, Sam was certain his stubborn brother could have kept quiet the whole hour, but now, not even Dean could keep quiet.

“Sammy, please, this itching is driving me crazy, just please, could you at least check that, I don’t know, if they are reacting from the lotion or something? Please, Sammy.”  
Oh Sam just loved how cutely Dean had started to learn to beg. That pleading truly deserved a reward.

“Okay Dean, but just so you know, if I don’t see anything off, I’m adding another addition to your punishment, are you fine with that?” Sam warned, before signaling to the car behind him that he was pulling over.

“Yeah, yeah, just check em.” Dean stopped squirming as Sam unbuckled his own seatbelt to turn towards Dean.

“Alright Dean, please hold up your shirt for me.” Sam yanked Dean’s shirt up and shoved it unceremoniously into Dean’s mouth as Dean opened it to question Sam. “Don’t drop it. Unless you want to eat salad to lunch.”

Dean only made a low whining noise as answer and strengthen his teeth grip around his shirt, making Sam proud over how much powers his orders now had for Dean. _“Of course, it’s still touch and go if he listens to me, but we’re getting there.”_

Having Dean hold up his shirt held two purposes. One, it made Dean stay quiet and two, it was another obedience lesson on the course of molding Dean into the perfect baby brother for Sam.

As Sam had suspected, Dean’s nipples were red, plump and just gushing for Sam to reach down and lick them. Sam could practically already taste them on his tongue, the softness in sharp contrast to the clamps around them..but they hadn’t reached that stage just yet. Now it was time for Sam to once again put great use on those theatre classes he had taken years ago.

“Dean, I don’t see anything wrong with your nipples. Yeah, they are red, but not more than you could expect, after all, this is the first time you have them on. Would you like for me to add some more lotion?” Sam asked, and cheered with sadistic glee in his mind as Dean nodded. 

“Alright, I’m going to remove them for just a short while to add more lotion, okay? Don’t drop the shirt.” Sam warned before removing the first clamp, enjoying himself tremendously with Dean’s muffled screams, carefully trying not to squash his own half-hard cock as he leaned forward to apply more of the itching cream on Dean’s nipple. Of course, Dean had no idea Sam was actually adding more fire to the flames instead of quenching it. 

“Okay, I’m putting the clamp back, try to stay still.” Sam said, being proud over how Dean didn’t try to disobey him but instead stayed still, his eyes slightly red, but Dean kept drawing in deep breaths, probably to not start crying. 

_“My sweet, brave little baby boy.”_ Sam cleared his throat to stop a fond smile from creeping up on his face. “Alright Dean, I’m gonna do the same for the other one.”

Sam did just as he said, getting to enjoy another drawn-out delicious pained moan from Dean. Sam made quick work with the lotion and clamp, eager to dish out the next “punishment addition”.

Now, Sam had quite a few sounds, all of them with slightly different purposes. Some to stretch and keep the urethra full, some to give the user a good dose of pain, some to turn the user into a mess of pure bliss. This one that he had planned to use on Dean was a bit of all three, especially in Dean’s current state.

“Okay Dean, you keep that shirt in your mouth, okay? I’ll be right back.” Sam got up to get the new sound from his duffel bag, almost skipping as he walked. He had to hold himself back to not use too many of his toys on Dean, not wanting Dean to be suspicious about why Sam owned so many sex toys. 

_“Oh well, I’m sure I can bullshit my way out of that conversation if I have to.”_ Sam thought as he rummaged through his very well-kept hidden stash of sounds and other fun toys. 

“Alright Dean, spread your legs for me, please.” Sam said as he opened the door on Dean’s side before crouching down slightly. “Remember I said I would add an extra item as punishment if I didn’t find anything weird on your nipples? Well, that’s what I’m doing now.”

Dean made a lot of noises, but dutifully kept the shirt in his mouth.

“Don’t worry, Dean, I’m not adding any clamps down there, just changing the sound.” Sam smiled reassuringly, unzipping Dean’s pants. “Now, please cooperate quietly, we wouldn’t want anyone to pull over to check what we’re doing, now would we?”

That made Dean stop struggling and obediently spread his legs, the horror of being found in such a compromising situation apparently enough to make him go along with what Sam was planning.

“Good job, Dean.” Sam praised, using his key to unlock the sound, slowly sliding it out, enjoying the slight twitching Dean did. He also admired the truly gorgeous sight of Dean’s caged cock, never getting enough of how red and cute it looked, trying and failing to get hard in the cage. Sam could practically see how it was straining against the walls, trying to rise up but failing miserably, keeping Dean in an acute state of arousal. Man, he was never getting tired of looking at it. 

“Alright Dean, time for your new sound. As you can see, this one has a slight extra addition at the tip.” Sam explained as he showed his brother the new sound. The sound was pretty much the length as the previous one, but without the bumps and instead equiped with another fun part, a vibrator at the top. The tiny egg at the top contained a battery and you could chose three different options for the vibrations; low, hard and random intervals. The egg was too big to go into a cock, but instead rested snugly on the sensitive tip, giving the user a truly earth rocking experience. Sam had only tried it once, and he had only been able to keep it on the low setting for ten minutes before pulling it out, spilling all over Dean’s unwashed shirt that he had used as jacking off material at that time. Sam couldn’t wait to see Dean’s face after having it on for forty minutes.

Sam shiver with anticipation as he slowly inserted the rod, trying to keep his hands steady as Dean’s cock hungrily swallowed the rod, only stopping when the vibrator part touched the tip. Sam quickly spun the vibrator so it would go on and off in random intervals, knowing it would drive Dean slowly insane getting short breaks from it before it turned on again 

“Alright Dean. Good job with keeping the shirt in your mouth, you truly deserve those hamburgers.” Sam smiled, still crouching down, hiding his erection with his position. “You can drop it now.”

“What--what is that round part?” Dean said suspiciously after he had spit out his shirt, leaving a big damp mark where his teeth had held it, eyeing the new rod with caution.

“Oh I’m sure you’re going to find out reaaal soon.” Sam chirped as he tucked Dean’s cock back into his pants and hastily zipped it. “Now if you excuse me, I’m going to take a quick leak.”

Sam cut off any of Dean protests by closing the door, before making a fast retreat to the nearby forest to have a quick alone time with his own hard-on, only spurred on by the moans and swearing he could hear coming from the car.

 _“Looks like the battery is still very much alive.”_ Sam chuckled and finally allowed himself to smile wickedly. He was sure Dean was going to give him some great auditory entertainment as he got back to the car. Especially with the new layer of itching lotion.

**Notes for the Chapter:**

> A/N: Apparently you can turn anything into a slow-burn fic if you try hard enough :D Man, I really didn’t plan this through when I started this *cough* ;^^; As always, leave comments or kudos if you’d like me to continue this story!


	6. Begging Is a Good Look On You

**Notes for the Chapter:**

> A/N: I have so many kinks and scenarios I want to write, but I have to include them in the right order, so both you and I have to wait a biiit longer until we get to some of the ideas/suggestion that people commented to me about(but I did include one in this chapter, hehe). But we’re getting there. Eventually. All good things comes to those who wait. Just ask Sam ;)  
> Once again, thank you so much to everyone who left comments and kudos, you are the main reasons I make time to write this fic. Here’s another one, please enjoy!
> 
> EDIT: This chapter is now beta'd by the awesome SanuraKitKat!

Sam looked at his watch. _“I guess thirty minutes should be enough.”_ Sam thought and started to walk back towards the car. At first he had thought of heading straight back to the car and Dean after he had jacked off to the memories of Dean all disheveled and begging, but then he had decided it would be much more fun to leave Dean alone in his own personal hell for a bit before coming back. Sam hummed happily as he opened the door and took in the lovely view inside the car.

The sight that welcomed Sam when he got back after his jacking off session in the forest was truly something captivating and something Sam would have killed to record and save for later. But now he just tried to carve every single detail of it into his mind.

Dean, was for a better use of the saying, looking **completely fucked**. He was drooling, a small amount of it on his shirt and some even on his pants. He was making small pelvic movements, like he was enjoying a lecherous fucking, but his eyes were puffed and Sam finally got to enjoy himself royally with staring at Dean crying, the tears leaving small streaks on Dean’s cheeks, which were flushed and puffed like Dean’s lips, probably from Dean gnawing on them as he tried to stifle his moans and whimpers and contain himself from drooling but failing spectacularly.

Fuck, Sam wished he could just trail his tongue and lap up those tears or gnaw those soft lips, enjoying the whimpers it would draw from Dean. But now he had to settle to just make a promise to himself that he would enjoy himself royally later.

“Oh wow, Dean, I wasn’t even that long gone, like, what, ten minutes?” Sam’s voice seemed to snap Dean away from his haze and Sam felt a rush by how absolutely fucking gorgeous Dean looked with a pleading, puppy look in his puffy, teary eyes as he slumped down on the driver’s seat.

“Sammy--pleas-ah-I-” Dean could barely form words and Sam could visibly see how the front of Dean’s pants were shaking, proof that the vibrator was most certainly doing it’s job.

“I see you’ve had some fun with your new toy.” Sam observed, having a feeling he could say pretty much anything right now and Dean wouldn’t remember it clearly, not with the nipple clamps, vibrator, the cock cage and the curse doing a hellishly good job of keeping Dean on edge. “Knew I picked a good one for you.”

“Sammy, mak-aah, please--sto-aah, it.” Dean moaned out, his head flopping forward as his body thrashed in his handcuffs from another wave of arousal. Sam was sure Dean would have cum several times already if he hadn’t been caged, but now, all he got was something close to dry orgasms, just empty fake orgasms that probably just doubled the frustration and arousal for Dean.

“It’s okay, Dean, I got you.” Sam cooed and used a tissue to gently clean Dean’s face, wiping the drool and tears away, smiling with satisfaction how Dean leaned into his touch. “I got you.”

After a while, the buzzing stopped, and Sam waited patiently until Dean’s eyes were a bit less foggy and his breathing became a little bit more even.

"How are you doing, Dean? Here, let me give you some water." Sam held the water bottle up to Dean's lips and smiled with how eagerly Dean gulped it down with greedy swallows. 

"That's better, right?"

"Sammy." Dean said in a raspy voice, swallowing hard and leaning his head back, closing his eyes as he tried to steady his breathing. "What the- fuck- I can't--"

"Tch, tch, Dean, what did I say about swearing?" Sammy clicked his tongue as he scolded Dean. "Seems like you need some more punishment."

"No, no, fuck, I mean, shit!" Dean opened his eyes wildly and then in panic swore again. "Sorry, Sammy, I didn't- please, I can't, I'm sorry, please don't-"

"Dean, calm down.” Sam chided Dean but then gently wiped some of the sweat on Dean’s forehead away. “I’m not going to punish you anymore right now. I leave that for when we get to the motel tonight.”

“Oh thank god.” Dean sagged down, relief clearly on his face and Sam felt positively giddy with glee how Dean wasn’t even questioning getting more punishment for his actions, but instead accepted them. _“Truly a bitch in the making.”_

“Dean it’s okay, I’m here with you. It’s gonna be okay.”

“Sammy, I don’t--this, hell, my nipples feel so itchy and that buzzing, it’s just, I don’t--I feel like I’m going crazy, please, Sammy.” Dean was pleading, his big puffy eyes locked on Sam, his desperation and honest raw emotions showing in them. Oh, Sam was loving this.

“I don’t understand Dean, you have to explain it better to me.” Sam tried to sound puzzled, loving how lost and desperate Dean sounded.

“Sammy, I can’t--”

“Try.” Sam said sternly, running a finger on the zipperline of Dean’s pants, enjoying the strangled noise his subtle actions drew from Dean. Sam wondered idly how Dean would sound if he actually took out Dean’s cock and started to jack him off. If his breathing would break off into hitched puff of inhales and exhales or if he would start to moan Sam’s name over and over, pleading him in that broken, crying voice... Sam debated switching his plan, but decided that he would much rather hear Dean describe his predicaments. “Dean, please, for my sake.”

“I...” Dean licked his lips, quickly glancing at his crotch, clearly fearing that the vibrator would go off again. “It feels, I don’t--It feels like my heart is trying to explode and I can’t feel anything and then suddenly I’m feeling everything, like how the cuffs are digging into my wrists, how my nipples are itching and it hurts when I move, but if I don’t then I can’t handle the fuc-the, um, the buzz in my cock and I can’t get away and everything is just too much and then I feel like I’m coming, like this high? And for a split second, it’s fine, I feel like I’m not here but then-it crashes down and I’m back and nothing is okay and I can’t, Sammy-” Dean inhaled sharply and buckled up slightly in his restraints.

Sam was feeling almost mesmerized by the small twitches and shifts he could see in Dean’s face and he could tell the exact moment the vibrator started to buzz again in the way Dean’s eyes widened and how his jaw line got even sharper from Dean clenching his teeth.  
Sam crossed his arms and pondered the situation for a moment, while feeling how his own cock hardened as he enjoyed the frustrated noises Dean was making. Dean description over his own hellish moment certainly hadn’t cooled Sam down either. His original plan had been to have Dean stuffed with the new sound on until they reached the restaurant roughly forty-five minutes from here, but he wasn’t sure he nor Dean could last that long, not with Dean moaning like this and Sam just wanting to drag him outside and stuff his ass with his cock, pounding him until he couldn’t sit for weeks. Still, Sam was very stubborn and he didn’t want to admit defeat and change his original plan of having Dean wear the vibrating sound until they reached the restaurant. Yet, he had to admit he wouldn’t be able to guarantee both their safeties if he kept driving with Dean right next to him as Dean kept making those desperate, needy noises that just made Sam want to ravish him there and there, to give Dean a real reason to scream and beg...

Sam mulled over the next step and had finally reached a decision when the buzzing stopped again, the random intervals keeping Dean nice and debauched on edge until the next round.

“Dean, I’m gonna make you choose.” Sam told Dean as he carefully wiped Dean’s cheek again as Dean had started to cry, fighting the urge to lick his fingertips.

“O-okay?” Dean voice was uneven, but he was slowly coming down from his torturous high.

“I understand you are having trouble with enduring your punishment quietly and I do think you are doing a great job of keeping it down.” Sam loved how happy Dean looked over the complement, his red eyes shining up slightly. “But I can’t drive if you keep distracting me like this. So I’m going to have to gag you.”

“You-what-no, no that’s not, Sammy, I won’t-”

“Dean, what you want or don’t want has nothing to do with this.” Sam cut Dean off with a harsh tone, leaving no room for arguments “You will be gagged, because I say so. Now, either you accept this or you don’t. Just remember, I will not hesitate to deal out more punishment if you chose the latter.”

“I--” Dean swallowed, his gaze flicker between Sam’s chin and his own crotch. “Okay. So what do I get a choice in?”

Sam exhaled, not even knowing he had been holding his breath. _“Good, this will speed things up a bit.”_ He stifled a smile and put on his more neutral expression again.

“You get to choose if you spend the next forty-five minutes until we reach the restaurant in the trunk or the backseat.”

“Why can’t I just sit here?” Dean argued back and Sam had to roll his eyes. As much as he loved dealing out punishment, Dean was really raking it up high and fast.

“Because Dean, do you really want people to see you gagged and puffy eyed when the cars and their passengers pass us by? Also, that’s one new strike for talking back, get three again and you’ll have another punishment.” _“And it will make this one look like child’s play.”_

Dean looked like he wanted to talk back, but then seemed to decide against it as the buzzing started up again. By the sound of it, this time it was the lower setting kicking in, leaving Dean panting and thrashing again, but not as incoherent.

“The-ah-the backseat.” Dean gasped out and Sam smiled, quickly getting up again.

“You got it, Dean.” Sam once again got up to fetch one more of his toys from his bag, this time choosing from his ball gags. He finally settled for one with black leather straps and a red 2 inches wide ball, knowing it would look absolutely gorgeous on Dean.

“Alright Dean. Remember, any talking back and you’ll get one more strike.” Sam warned as he saw Dean open his mouth, guessing it wasn’t exactly to gush excitedly over Sam’s choice of gag.

Dean eyed the ball gag but didn’t say anything, unconsciously licking his lips and Sam was once again acutely aware of his own-half hard on. _“One step at a time.”_ Sam was sure he would have those plump lips wrapped around his cock later today and for now, he just had to (sadly) ignore his own desires and focus on the task at hand.

“I know it looks big but I’ve seen you stuff your face with hamburgers, so I’m sure this won’t be that hard.” Sam joked, trying to ease the situation slightly. “Now open up, remember, the quicker we get this done, the quicker we’ll get back on the road, yeah?”

“I--It’s just until we reach the restaurant?” Dean asked and Sam decided to cut Dean some slack and not punish Dean for that remark, it was an honest question after all.  
“Yeah, you can’t eat with this on, right? Don’t worry, Dean. You trust me, right?” Sam made his voice softer. “You know I’m only trying to help you. I know my..methods might seem weird, but I promise, I’m only trying to help you.”

Dean was looking at Sam, and for a split second Sam was worried Dean had seen through his act and would call him out, but then Dean exhaled and slumped back in his seat.

“Okay. Just..drive carefully, okay? No fast and furious with my baby.” Dean said with a small smile tugging at the corner of his lips.

Sam snorted and leaned forward, lifting the ball gag to Dean’s face. “Of course not, Dean. Now, open up. Please.”

Dean rolled his eyes but then opened his mouth wide and obediently so that it made Sam bite the inside of his cheeks to not smile like the proud brother he was.

Sam held the ball against Dean’s mouth and urged Dean to open up just a little bit more as he gently but steadily kept pushing the ball inside Dean’s mouth until the ball was tugged nicely and snuggly behind his teeth, keeping Dean’s mouth wide open. Sam quickly snagged the straps tight, adding a little lock to it on the back of Dean’s head, to make sure Dean wouldn’t try to open it, as he would only be handcuffed behind his back in the backseat. Sam had played with the idea of strapping Dean into an armbinder, but decided that the added ball gag was enough addition for now.

And it was a gorgeous addition. Sam couldn’t help but slowly caress Dean’s face between his palms, marvelling at how stunning the red ball looked between Dean’s plum and strained lips, and how the straps slightly digged into Dean’s flushed and blotched cheeks, making Dean look both helpless and absolutely gorgeous at the same time. And Sam simply couldn't get enough off those red, puffy eyes that were looking at him with so much trust.  
He really had the best baby brother in the whole world. And he was most certainly done with sharing him with angels and demons.

"Alright, looks like it's not too tight. Are you feeling okay?" Sam got to caress and probe a bit more on Dean's face under the pretext of checking that the gag wasn't suffocating Dean.

"Nnnng." Dean tried to reply, but everything that came out was just a muffled sound, much to Sam's approval.

"Good." Sam nodded and swiped some sweat away from Dean's eyebrows. "Alright, let's get you in the backseat then, yeah?"

Sam waited until Dean nodded before leaning around Dean to unlock the handcuffs, inhaling deeply for a second, enjoying the close proximity and the smell of Dean before unlocking one of the cuffs before leaning away again, motioning for Dean to get up.

"Try anything and it will be another strike." Sam warned Dean, but observed with pride how Dean obediently got out off the seat slowly without making any sudden movement, supporting his wobbly legs with a tight grip on Sam's arm.

"Okay, I'm gonna put an arm around your waist, Dean." Sam said before tugging Dean closely, enjoying the smell of Dean, the air filled with the smell of Dean's sweat and musky scent that Sam loved so much.

Dean only made some small noises and clung desperately to Sam, his eyes wide and Sam knew without looking that the vibrator was on again, affecting Dean so much that he staggered in walking the few steps to get to the backseat, and would have dropped like a log on the backseat if Sam hadn't supported him.

Sam quickly cuffed Dean's hand together and frisked Dean's back pockets, removing the clip Dean kept there for emergency situation. Sam doubted Dean would have a clear enough moment to try to pick his handcuffs, but he didn't want to risk it anyway. Then he fastened the two seatbelts around Dean to keep him from falling off the seats and stuffed his jacket under Dean's head to give Dean some slight comfort. Sam knew Dean was going to need it.  
Dean had been too engrossed in his own torturous pleasure to actually notice what Sam was doing, his eyes closed and his hips bucking as he desperately and to no avail tried to get some relief. Sam gently dragged a hand through Dean's tousled hair, getting one last look of his perfect baby brother before closing the door, drawing in deep breathes as he collected himself, trying to calm down enough to drive.

"Breathe in, breathe out." Sam muttered to himself, getting into the car and adjusting the back mirror so he could see Dean's face. Both in order to sneak quick glances at Dean's gorgeous crying and suffering face, but also to make sure Dean wasn't suffocating or otherwise hurting in a way Sam hadn't planned.

"Alright, Dean." Sam turned the key and allowed a wicked smile to cross his lips. "Time to hit the road again." He didn't wait for an answer before backing up on the main road, feeling his heart beat in anticipation over how utterly wrecked Dean would look after another forty-five minute of having the clamps, vibrator sound and cage keeping him on edge. If Dean looked this disheveled after roughly forty minutes, how bad would another forty make him look? Sam couldn't wait to see.

**Notes for the Chapter:**

> Please leave kudos and/or comments if you'd like me to continue the story!


	7. Communication Is Key and You Keep Locking Me Out

**Notes for the Chapter:**

> A/N: This story now has over 10k hits and way over 350 kudos (???), not to mention the great amount of comments?? Wow, I’m truly speechless, I never would have even imagine this when I uploaded the first chapter. Thank you so much to everyone who left kudos and comments, it’s all thanks to you that I keep updating this story as often as I do <3 Here’s another one for the road! This chapter took a bit longer and got waay longer than I anticipated, mostly cause I didn’t want to split it into two parts and leave you with a nasty cliffhanger, so I hope you’ll enjoy it ;) 
> 
> Slight spoiler; this chapter contains voyeurism, since yes, they are outdoors, but no, no peeping Toms stop by to help/watch Dean and Sam. Just wanted to point that out in case someone needed a heads up :) Now, on to the the real reasons you are here, the chapter!

Dean in the backseat was great car company. Now, Sam got to drive while listening to the quiet noises of Dean suffering in the backseat and once in awhile steal a quick glance at his flustered face.

Sure, a vibrating butt plug would have been the cherry on top, but Sam guessed that would be for another road trip. Right now, it was enough for him to hear the small gasps and muffled distressed noises Dean was producing, all while the handcuffs keeping his arms behind his back and seatbelts around his body kept him in one place.

Sam also felt a small pang of arousal every time he hit a pothole and Dean made the most exquisite noise as it probably made the clamps and rod shifts ever so slightly, reminding Dean once more how little control he had over his own body.

Sam had to fight the urge to risk to jack off in the car, trying to tell himself it was worth the wait, beside, he really didn’t want to risk it all by doing something as stupid as crashing right now.

“You’re doing so great, Dean. Only a bit more.” Sam didn’t know if the groan Dean uttered was in response or if it was only the vibrator kicking in again, Sam could (sadly) not hear the buzz over the car engine. 

Sam knew his baby brother was in an acute state of arousal. The nipple clamps must be itching like hell, the extra layer of itching lotion probably turning Dean’s breast into an area of pure untouchable agony. The curse was also still pulsing through his veins, keeping Dean aroused and listless, his cock throbbing and desperately trying to get hard, but failing thanks to the cock cage. And the sound, shifting and vibrating when the egg was on, sending spikes of heat and stimulation in vain to Dean’s brain. To be fair, the gag was probably the least of Dean’s problem, but it was probably not helping at all, leaving Dean’s mouth aching and him drooling on Sam’s jacket. Sam wished he could have those lips around his own cock, feeling Dean’s teeth scrape slightly against the shaft as he plunged deep inside Dean’s hot mouth, not caring at all over the choking noises Dean made...

Sam bit his lips. _“Fuck, I need to think about something less sexy. Old granny pants. Bobby in a speedo. Dean sucking Cas off.”_ That last thought made him slam his foot down on the gas, making the car roar and Dean to whine higher.

“Ah, sorry, sorry, Dean.” Sam laughed, trying to regain his good mood. “Just a little bit more now until we’ll get you your burger and fries!” Sam could already see the signs showing how he should drive to get that sloppy fast food Dean loved so much. 

“But first I have to stop real quick to fix you up a bit.” Sam said as he signaled that he was pulling over.

Sam didn’t explain any further, only stepped out of the car, getting a blanket from the trunk that he then used to pull over Dean’s upper body and head, covering Dean blotched and devastated face completely.

“We don’t want anyone to see you like this right? Just hang in there while I order, okay? It will probably be a bit uncomfortable, but I’m sure you’ll be okay.” Sam smiled, grateful he seemed to have timed his stop with one when the vibrator was on, making Dean completely out of it and unable to focus on anything. 

Sam only spent the minimum time as possible at the fast food place, ordering at the drive-through, a meal set for Dean and a salad for himself, tapping his fingers on the steering wheel, trying to not draw any suspicion to himself or the conspicuous lump in the backseat. 

He exhaled in relief as he got the food and was allowed to roll out on the road, filling the car with the smell of fries and hamburgers. Apparently Dean could also smell it, since the noises he made turned up one notch.

“Yes, yes, hang on Dean, I’m just going to find a rest spot first.” Sam chided, also eager to stop and check up on Dean and see in what state Dean was in. Sam did have a plan for what he wanted to do to Dean next, but he knew that if Dean was too out of it he might have to rethink his plans a bit.

After a few agonizing minutes, Sam finally got to pull over, the rest place slightly secluded and vacant, just perfect for what Sam had planned.

“Alright, Dean, time for some food and a break!” Sam declared after stopping the car. 

Sam opened the car door and slipped the blanket off Dean and he had to admired how gorgeously disheveled Dean looked for a moment before he helped Dean sit up in the car, unclasping the seat belts. Dean’s face was wet with sweat, tears and drool and his puffy eyes were tightly squeezed shut, perhaps in a childish and pointless attempt to stop the torture he was going through.

Well, Sam was having none of that.

“Dean, open up your eyes.” Sam chided as he gently unlocked the ball gag. “I need you to try to open up wider so I can remove the gag.”

Dean made a whining noise and shook his head slightly, making Sam click his tongue impatiently and flicking Dean’s nipple as a warning to behave.

“Open. Up.” Sam urged sternly and Dean seemed to get the hint and opened his red eyes, his beautiful eyes even more perfect with lots of red around them. Dean tried his best to open his mouth more to make the gag plop out and with a bit of help from Sam, it did just so. 

“There, that wasn’t so hard, right? I’m going to turn off the vibrator now, so be still.” This time Sam didn’t have to say it twice. Dean obediently went perfectly still, even in his wrecked and disoriented condition clear enough in his head to know that this was something he very much wanted. 

Sam made quick work of turning the (for the moment) still vibrator off, removing the battery but leaving the sound in. Then he uncuffed Dean from the handcuffs, deciding Dean was behaving good enough for him to be allowed to eat with his hands.

“Alright, Dean, I’m going to help you to the table and then you get to eat, okay? I bought your favourite greasy burgermeal.” Sam said with a cheerful tone, helping Dean to walk to the table, as Dean’s whole body was still shaking slightly from the earlier suspension ride.

Sam had to admire his brother. He had knew Dean was quick to recover from traumatic events, being on enough hunting trips to know that for a fact, but even he was impressed by how quickly Dean collected himself after he turned the vibrator off. Sure, Dean was still on edge, his whole body stiff and restless, but his face and manners was much calmer than when Sam had inserted the vibrating sound and there was only a slight degree of puffiness and red around Dean’s eyes, not too different from the look Dean got after a whole night of partying. And there was certainly nothing wrong with his appetite, if the way Dean was wolfing down his burger was any indication. 

After Dean had finished stuffing his face with junk food and slurping the last of his soda, he sat quietly as Sam finished his salad, making new patterns in the table with his nails. It seemed like Dean was collecting himself after the exhausting car ride he had just taken and Sam saw no reason to not take his time with his own food before he put the next part of his plan into action. After all, the concentrated dose of diuretics in Dean’s soda he had put in earlier was surely going to speed things up soon enough. 

Sam had barely finished his meal before Dean started squirming and it only took a few minutes of him pretending to do some research on his phone for Dean to speak up.

“Sam, I’d, um, I’d like to pee.” Dean hesitated and then quickly added, “please.”

Sam had first thought of maybe being a bit more harsh and force Dean to keep it in a little longer, but that please made him feel so proud that he couldn’t contain his happiness.

“Well, Dean, since you are asking so nicely.” However, that didn’t mean he wasn’t going to make Dean earn his privilege properly. “But you know the drill.”

“What are you saying, Sammy?” Dean got a cautious look on his face, and Sam knew he had to play his cards right to get what he wanted without having to spell it out.

“Well, you know, you do have one strike right now, and also one punishment to receive when we get to the motel, but how about a little game? If you play your cards right, I might scratch that strike.” Sam smiled sweetly, hoping Dean would take the bait.

“What kind of game are we talking about?”

“Well, your blowjob in the car wasn’t really that great, but I was thinking of giving you a second chance and well, if you don’t spit out my come like earlier, I’d be willing to not only let you pee, but also scratch that earlier strike.”

“Uhuh.” Sam was overthrilled that Dean seemed to be seriously going along with his scenario. “And what’s the catch?”

“The catch is that if you fail and don’t manage to swallow it all, I’ll give you your punishment right here and not at the hotel. But, either way, you’ll get to pee.” Sam had to look at the table for a moment to fix his facial expressions. Dean didn’t have to know that no matter how he did, this was a win-win situation for Sam. Either way, he still got a blowjob out of this. 

Dean mulled over the ultimatum, but then he shifted slightly and it looked like his bladder got the last word. “Okay, but do we really have to do it here?” Dean looked around, clearly uncomfortable by how close the main road was to the rest spot. 

“Don’t worry, this table is behind the car, as long as no one is pulling over, they won’t see us.” Sam said with a winning smile, pointing between his legs. “Besides, if you crawl under the table, the risk will be even smaller.“

Dean grumbled but seemed to realise he really didn’t have anything to argue with if he wanted to pee, so he quickly scrambled under the table and positioned himself between Sam’s wide spread knees and Sam had to stifle a laugh on how eagerly Dean’s actions seemed, especially if you didn’t know how much pain and agony Dean was in. Sam knew Dean surely wasn’t feeling to great and he was probably really wishing to avoid the earlier experienced of having to hold it in for over an hour in that condition. 

“Alright, Dean, I want you to take out my cock and don’t start bitching, alright?” Sam could see that Dean was making a disgusted face, clearly not comfortable with Sam’s choice of words, but he only muttered something that Sam didn’t catch and didn’t bother to make a fuss over, to eager to get Dean’s hot mouth around him again.

“Alright, Dean, now I want you to place your hands on the bench and don’t move them until I tell you too.” Sam ordered as Dean had freed his half-hard cock from its confinement. 

Dean didn’t say anything, but placed his hands as Sam had ordered him to and then started to suck Sam off.

Sam could tell Dean was doing his best to get this over quickly, moving his head back and forth in quick motions, probably mimicking what some chick had done to him that he had enjoyed. The problem was that that wasn’t at all what Sam wanted.

“Dean, I want you to take in a deep breath and let me take the lead.” Sam kneaded his fingers into the back of Dean’s hair, gently guiding Dean off his cock. Dean looked at him with a puzzled expression but complied.

As soon as Dean had inhaled, Sam gently started pushing inside, urging Dean to open up even more than he had ever done before.

“Control your gag reflex, try to relax your jaw and throat. And don’t you dare move your hands from the bench.” Sam ordered and gently started to rock Dean’s head back and forth so his cock slipped with wet and sloppy noises even further down Dean’s throat, feeling the hot sensation of Dean’s mouth engulfing more and more of him. Sam kept going deeper and deeper for every thrust.

Every now and then he withdrew so his cock was only in Dean’s mouth, urging Dean to draw in raspy breaths through his noses, but never allowing Dean to close his mouth, enjoying himself tremendously on how quickly Dean followed his instructions. Sam was enjoying himself even more than he had done earlier, finally being able to enjoy fucking his brother leisurely, like he had all the time in the world to enjoy Dean wet, hot mouth, and the tight, smooth sides of his throat. 

“You’re doing so great, Dean. You are so much better already.” Sam praised, using his free hand to wipe away some tears that had escaped from Dean’s eyes. “So good for me.”

Dean was making some noises that Sam thought probably meant Dean was disagreeing but paid him no mind, too engrossed in how great Dean’s mouth and throat felt around his mouth. Sure, Dean still couldn’t take all of him, but he was a quick learner and he was already a better mouthfuck than the time before.

Sam kept this pace for a bit longer, until he felt that he had had enough of this slowburn and he quickly started speeding up, completely ignoring the noises Dean did and got a kick off the noises Dean made as he tried to keep up with Sam’s pace and not throw up. Sam rewarded Dean’s effort by giving Dean a fair chance to swallow all his thick cum as he came, keeping his cock in Dean’s mouth more than his throat. 

_“I’ll get more chances for choking Dean with my cum later.”_ Sam thought with a smile tugging at his lips as he watched Dean struggling to swallow his cum.  
Dean was having a hard time getting Sam’s copious amount of sperm down, clearly not liking the taste at all. Well, Sam had no doubt Dean would come to love it eventually, as Sam had planned for Dean to taste it several times a day in the near future. 

“Oh, Dean.” Sam shook his head in disappointment as Dean made a distressed noise and spit out the rest of Sam’s cum. Lucky for Dean, nothing of it landed on Sam but instead on the ground. “And you were doing so great, too.”

“Oh, please, just--” Dean glared up towards Sam, but Sam’s icy stare stopped him mid-sentence and he clasped his mouth shut, using his sleeve to wipe off the rest of Sam’s cum.

 _“That’s right, Dean, keep your pretty mouth shut if you won’t do something useful with it.”_ Sam wasn’t really too upset over how the blowjob had ended, sure, it would have been nice to see Dean swallow his thick load, but this way, he got to deal out more punishment, so he wasn’t too unhappy about it. 

“Alright, Dean, the bad news are that you’ll have some fresh punishment waiting for you before we get back on the road.” Sam told Dean as he swung his leg over the bench, motioning for Dean to get up too. “But the good news are you’ll get to pee before it.”

“Great.” Sam decided to ignore that comment, still feeling satisfied after getting a blowjob.

Sam made quick work of unlocking Dean from the sound, before he cuffed Dean to a nearby fence, telling Dean that if he tried anything while Sam left him alone he would regret it. 

“Yes, yes, I know, you’ll punish me. Got it the first time.” Dean waved his hand and Sam had to still his hands to not slap his brother, deciding he would just add that to Dean’s ongrowing list of punishment.

“I’ll be watching you the whole time.” Sam warned before he walked backwards to the car, making sure Dean wasn’t trying anything. Sam felt great pride swell in his chest over how obediently Dean did as he said, only keeping his hand on his cock to a minimum, probably already tried yesterday to jack off with the cock cage and fail miserably and not doing the same mistake twice.

“Did you enjoy your pee-pee time?” Sam asked jokingly as he got back from the car with some new toys and he didn’t pay Dean’s guarded expression much attention, too eager to get to punish his baby brother again. “I really hope so, cause it’s time for your punishment.”

“What’s in the bag, Sam?” Dean folded his hands over his stomach after Sam released the handcuffs, his elbows resting in his hands, Sam guessed Dean would have tried to cross his arms but the clamps too painful for it to work, making Dean fold his arms like that instead.

“Oh don’t worry, Dean, you just sit down on the bench so I can insert the rod again.” Sam said as he placed the bag on the table, before motioning for Dean to sit down. “I know what I’m doing, Dean.”

“That’s not-” Dean drew in a deep breathe, his jaw jutting out and his hand jabbing towards Sam. “Fuck it, Sam, I’m not playing along with your stupid games anymore! I’m your brother, not some fucking sex slave!”

“Dean.” Sam growled and clenched his fists, feeling his heart rate quickly rising. He cursed himself for not paying more attention to Dean’s emotional state earlier. “Careful now.”

“No, fuck no, I ain’t playing this anymore! Sam, this has gone way out of hands, you can’t just tell me-”

Sam straightened up and dug his fingers into Dean’s scalp, forcing Dean to look up at him and putting his other hand over one of Dean’s nipple, pinching it harshly with the clamp.

“Yes. I. Can. Dean.” Sam yanked harshly on Dean’s hair for every word, not bothered at all how much it must hurt. There was a limit to how much he would allow Dean to act out, and this was definitely crossing it. “Don’t go getting on any high horses now.”

Dean was practically snarling at him and apparently running high on adrenaline so the nipple tweaks barely produced a twitch in his face. “Like the one you are on?”

Sam snorted and forced Dean to bend his head even further up, playing their heights difference to his advantage to the fullest. He kept Dean there for a moment, just eyeing him intently without saying anything before letting go and stepping back, his face a perfect blank expression.

“You know what, Dean?” Sam held up his hands with his palms facing his brother. “I’m done with your bitching. If you don’t want to play by my rules, then fine. Don’t. But don’t expect me to help you out anymore either.”

Sam turned around and headed to the car, getting inside and slamming the door without another word, boiling up and having a hard time containing his rage.

 _“I fucked up. I fucking fucked it up!”_ Sam tried to take deep breaths in order to get his emotions under control, but he was too upset over his own failure to succeed. He knew he had to get out of the car and overpower Dean with sheer strength in order to continue his plan, but he needed a moment to process the disappointment over his fuck up. Sam had hoped he would have been able to trick Dean into submitting himself willingly. The thrill and exhilaration of fooling Dean into following his every demand and whim while believing Sam was only doing it for his own good was so much better than having to break Dean and make him so desperate to his own needs that he would whatever Sam told him to do. 

Sam was currently debating if he should bring out the stun gun when he heard the car door. Sam’s eyes widened in surprise as Dean slumped down in the passenger seat. Sam didn’t dare to speak and just waited for Dean to make the first move, having no idea what would happen next. It didn’t look like his brother had figured out that Sam actually knew how to undo the spell and Dean’s unsure and broody expression didn’t indicate that he was here either to wrestle the key to the cock cage from Sam.

“I’m sorry.” Sam wasn’t sure he heard right so he had to ask Dean to repeat himself.

“I’m sorry, Sammy, really. I keep screwing up and making you mad and,” Dean was fiddling with the door handle now, his voice low and he kept clearing his throat, “I don’t mean to put this much pressure on you. And I don’t really get all your rules and--and orders, but I do trust you.”

“I’m sorry too for lashing out like that, Dean. But, you know I’m only doing this for you, right? To not make you spin out and well, go crazy.” Sam was treading carefully, cautious now as he tried to undo his earlier actions and of course, lying through his teeth, but Sam had been lying for quite a while about quite a lot of things, so he had would say he had become pretty good at it by now.

“Yeah, I know, I know. And look, I’m sorry and I swear I’m not trying to make this all about myself again, but, you gotta, like, cut me some slack here too, okay?” Dean tried to force a smile, but it didn’t quite make it. 

“I know Dean, but you also know that if you want my help, you have to play by my rules, right?” Sam decided to play the understanding but stern brother part. 

“I do, Sam, I do. It’s just--so messed up.” Dean was twiddling with his hands, something Sam rarely saw him do, but he decided to not mention it, instead push a bit more.

“Dean, this will be the last time I’ll be this understanding, there won’t be a next time. Do you understand me? Cause I can’t help you, if you ain’t willing to help me, well, help you.” Sam was looking at Dean with a stern face, observing every flicker of emotions Dean tried to hide. Distrust, desperation, anger, lust, despair, frustration and trust. So much trust. Sam decided to push one more button before leaving it up to Dean to decide how this would play out.

“You know Dean, if our position were reversed, I’d trust you without a second thought. You know that, right?” 

Dean’s head jerked back slightly, and Sam watched in satisfaction how Dean looked guilty over having doubts over his little brother’s motives. _“Good, looks like I still got some acting skills left.”_

“I know, Sammy. I’m--” Dean swallowed and the he slowly lifted his head to look Sam directly in his eyes. “ Of course, I trust you.”

“Are you sure? Cause you sure as hell ain’t acting like it. Maybe we should just split up instead of-” Sam managed to sound the perfect mix of hurt and unconvinced and Dean bought it completely.

“No, no, Sam, I’m so sorry, I don’t know what came over me, please!” Dean frantically grasped Sam’s arms, his eyes pleading with desperation, clearly terrified over the mere thought of being left alone with the curse clouding his thoughts and actions. “Please, I promise to be good.”

“Prove it then, Dean.” Sam said and he felt his earlier confidence rush back when Dean nodded eagerly. 

_“Looks like I got a second chance”._

Sam was happy that the whole fight had been solved as smoothly as it had, but it had been closer than he had liked for everything to go completely sideways. From now on he would have to make sure to keep Dean more on edge and not allow him to gain such a clear moment like that again. He was lucky Dean trusted him as much as he did, but Dean was also smarter than he looked and Sam really needed to mold Dean faster, but also with a sterner hand than he had did before. Also he had a gnawing suspicion he had been too rough on the escalation of the sex toys, but he couldn’t say he regretted it, the noises and expressions his baby brother had made during them was something he would never forget. 

“Alright, Dean, your punishment is simple. I’m going to use this on you for ten minutes and you are not allow to beg or plead for me to stop. Got it?” Sam poured a generous amount of lube in the fleshlight, making sure it was all nicely lubed up to get Dean all hot and bothered.

“Got it.” Dean swallowed, his legs on either side of the bench, his fingers nervously drumming on the table, the other hand clutching the bench. Sam had inserted a new sound after their talk in the car. This one was slightly bigger than the one before, and with slight bumps that got bigger as the sound went on, stretching Dean’s cock nice and tight, just as Sam wanted. However, Sam had removed the cock cage and instead placed a steady tight cock ring around the base of Dean’s cock, keeping Dean’s cock long and hard for Sam to squeeze inside the fleshlight.

“Well then Dean, I’m going to start the clock now.” Sam tapped the phone, letting the timer go off, counting down from 10 minutes.

Dean was trying to take deep breaths and acting like this wasn’t hard at all, but his dick was peaking and his stomach was heaving and his thighs muscles were clenching and unclenching almost on their own volition.

“Remember, for every time you beg I’ll add ten slaps.” 

“Ye-yeah.” Dean nodded, his hands gripping the table edge and bench in a death grip. 

“Okay, here we go.”

It didn’t take long for Dean to slowly fall apart, for his gasps and moan too become too many for him to bite back. After a few minutes, all promises and shreds of dignity had been stripped away, thanks to the ruthless pace Sam set, his hands never stopping squeezing the fleshlight around Dean’s hard cock. 

“Sammy--pleasepleasepleah--no-don’t--please-” Dean was desperately clinging on to Sam’s shirt, his head almost touching Sam’s shoulder every time he swung forward, his back hunched and his whole body shaking, his eyes wild and unfocused and he kept swallowing unconsciously, but he didn’t manage to keep his mouth shut for long. Sam was getting hard hearing how incoherent his baby brother was getting and how he kept forgetting he was forbidden from begging.

“Dean, that’s twenty more. And you haven’t even lasted five minutes yet.” Sam squeezed the fleshlight harder as he pushed it upward, his dick twitching as Dean’s hips moved upward with it and then with satisfaction listen to Dean’s broken sob as he slammed it down, forcing Dean to sit down again.

“I can’t--too--too much--Sammy--” Dean kept whining, the hand not crunching Sam’s shirt fluttering down, but Sam enclasped it in his free hand before it manage to reach too far down. 

“You need this, Dean.” Sam placed light kisses on Dean’s knuckles and fingertips, slowing down to an agonizing pace with only slight pressure around Dean’s cock, knowing the pace would be no better for Dean than the earlier harsher pace, but it would keep Dean more coherent. “Trust me, this is good for you.”

“It’s good for me.” Dean repeated in a slurred voice and Sam’s heart skipped a beat and he almost lost his grip on the fleshlight before he snapped out of it. He truly hadn’t expected this sudden confession, but who was he to let such a gold opportunity go wasted?

“Yes it is, Dean.” Sam cooed and squeezed Dean’s hand tighter, anchoring Dean to his touch. “You trust me, right?”

“I--I trust you.” Dean gasped out, his head now resting on Sam’s shoulder, his uneven breathe tickling Sam’s neck, his both hands squeezing Sam like he was afraid he would shatter apart if he let go. “I trust you, I trust you, Sammy. Please, Sammy, please.”

“What do you need, Dean?” Sam kept up the same tempo, but started to alter between his squeezes, adding in some tighter ones between the loose ones.

“I need, I need--” Dean made a small hiccup and Sam wanted to yank his head back and bit his neck and claim him right there and then. “Sammy, please, I need to come, please please let me come.” 

Sam knew that there was no way for Dean to actually come, to spurt all over Sam’s dark jeans, not with the sound snuggly inside him and the cock ring squeezing the base tight. But that didn’t mean Sam wasn’t going to waste such sweet begging.

“Well then, Dean.” Sam picked up the pace as he got close to Dean’s ear. “Come.” He commanded before he squeezed tight down on Dean’s cock.

Dean’s reaction was instantly. Sam could feel how Dean’s whole body shook against his and Dean made a strange choking, strangled noise when his hips buckled forwards and the hand in Sam’s seemed to try to break his bones as Dean came. Of course, with the sound in, Dean couldn’t ejaculate, but it was downright adorable how his cock had still desperately tried to, being pushed so on edge that even when it was impossible, his body still tried to force him to ejaculate. 

Sam basked with pride over Dean’s effort to comply with his command as he quickly caught Dean from dropping on the ground. Apparently all the excitement and events had been to much for Dean and he had passed out after his dry orgasm. 

“I’m so proud of you, dear baby brother.” Sam gently swiped some sweat from his unconcious brother’s face before kissing his face tenderly. “You’re making such great progress.”

Sam knew he was going to have to punish Dean severely for not completing his punishment, but he didn’t want to wake up his baby brother, knowing he would have more privacy in a hotel room than here for the punishment he had planned and he didn’t want any unwanted attention.

Sam felt his lips stretch even further as he picture how much fun he was going to have in just a few hours with Dean, his baby brother that was now trusting him wholeheartedly. 

He sent a mental thank you to the witch as he carried the unconscious Dean to the car. 

_“Gonna have to swing by the store to buy some new toys.”_ Sam thought and then remembered that he had forgotten to count how many times Dean had begged, but he decided he would just round it up to a nice number. He smiled devilishly to himself as he carefully opened the car door. _“It’s not like Dean will remember anyway.”_

**Notes for the Chapter:**

> A/N: Phew, I hope you enjoyed reading this rollercoaster of a chapter! I wanted to convey sort of a “point of no return” moment, of Dean now fully trusting Sam, as his sole anchor in his own special hell. Too bad he hasn’t realised Sam is actually his tormenter and not his savior... Next chapter will start the longer punishment session! I assure you all, it’s only going to get more intense from here on ;) I got some great ideas for the next part, hehehe...
> 
> Please leave comments and kudos if you want me to continue the story! I assure you, every kudo and comment counts! :)


	8. Behind closed doors

**Notes for the Chapter:**

> A/N: I’m so sorry for the long wait, so much stuff has gone on in my life, ugggghhhh!! ;;;;; But woow, I’ so happy over all the comments and kudos this story keeps getting! Thank you so much for everyone who leave comments, it really helps me a lot and motivate me to continue writing! (Srsly, over 450 kudos??? I’m!!!) Now, I got a really helpful feedback from steeleye1 about sounding and ejaculation, you should all check out their comment in ch 7, for the sake of the plotline I won’t rewrite the last scene, but you should all check out the recs and links they send me!! Especially if you are into some darker kinks than I include in this story ;)  
> I’m not gonna go into details about what’s going on in my life, but I will assure you all that no, this story is not dropped, I am definitely planning on continuing it! Can’t say how often I will update, but I gonna try my best to not keep you hanging for this long again! And I have so many great ideas and punishments that I'm planning to include! Like, enemas, expanding butt plugs, (more) sounding and ball torture, to just name a few! But yeah, all in good time! Well then, enough about that, on with the story! ;)
> 
> SPOILERS: This chapter includes spanking, this has been your only warning :D
> 
> NOTE: I haven't checked it as much as I usually do, so excuse any mistakes, they will be fixed on a later date when I got more time, but I really wanted to give you all a new chapter asap!

Sam had chosen to stop driving when he hit the first larger city his gps told him held some decent sex shops. It was in no way on the way to where they had planned to go but Sam had a feeling that that wasn’t what Dean was going to ask first about when he woke up. 

Sure, Sam was eager to go buy some new toys, but he was far more eager to punish Dean so he decided he would have some fun before he went on a different kind of hunt. Especially since Dean had raked up some pretty high punishment. 

Paying the motel owner in cash and giving up a fake name had been the easy part. The harder part had been to drag his unconscious brother up the stars and into the room without being noticed. Sam really didn’t need any meddling passerby asking too many question. Not when he was this close to finally getting Dean all to himself.

Apparently the whole fleshlight had been too much, even for Dean, as he had yet to be conscious enough to bitch about whatever Sam was doing, which Sam certainly wasn’t complaining about. Not when he was preoccupied putting Dean down on the bed.

“Don’t worry, Dean, I’m gonna make sure you’re properly awake when it’s time for your punishment.” Sam smiled as he gently ran a hand along Dean’s tousled hair before starting to dig out the cuffs he had in his bag.

Sam made quick work of laying out the restraints he needed to get Dean in a nicely tied up position, some cuffs, armbinders and spread bars and then some nice long ropes to secure that Dean wouldn’t be able to wiggle around too much when Sam dealt out his first punishment, which was some good ol’ fashioned spanking.

Sam had a long list he was going to methodically go through with his baby brother, but he wanted to start with the one he had been dreaming about doing ever since he had realized his desire to dominate Dean. Spanking Dean’s round and plump ass until it turned an angrily shade of red and making it hard for Dean to sit for days. For this first spanking experience, he was only planning on using a wooden hairbrush and his hands, but later on he was going to let Dean get a taste of some whips, but for now, he wanted Dean to experience his first spanking in a more traditional way, like the naughty boy he had been. 

Sam started to strip Dean, being as cautious as possible to not wake him up. It would be a shame if Dean started to stir awake without being restrained, since Sam was certainly it would be much easier to make Dean pliant if the first thing he experienced was pain.

Sam made quick work of his brother's pants and shirt, admiring Dean's plump and strained nipples. The clamps had truly done a remarkable job in messing Dean up and it could be seen clearly on the shade of red the nipples showed and Sam felt a chill down his spin over just the thought of the cry of agony Dean would make as he unclasped them. But before that, he needed to put Dean in a proper position to punish it.

For now, Sam decided Dean would be keeping his boxers on, so he gently turned Dean on his side, as to not press his caged nipples and groin into the mattress as he placed Dean so he wouldn’t tip over as he carefully pulled Dean's arms into the armbinder, the smooth dark fabric matching perfectly with Dean's lightly tanned arms.

"So perfect for me." Sam whispered, fighting the urge to pepper Dean's naked shoulder with kisses and focused on tightening the clasps on the armbinder, making sure Dean's arms were properly restrained.

Sam then trudged a pillow below Dean's stomach, leveling it so when Dean tipped over that not much pressure landed on his nipples, but instead put Dean in a very submissive position, with his ass properly in the air after Sam pulled and parted his legs in the perfect position. After that Sam placed the spreader bar between Dean's knees, adding a pair of cuffs to Dean's ankles and the bed frames, before completing immobilizing Dean with some ropes to secure him properly in place. It wouldn't do for Dean to try to wiggle his way or hurt himself trying to escape his punishment.

And Sam would make sure there was no passing out this time. It had worked out perfectly for Sam to have Dean unconscious for this part of the journey, but now when he finally had his baby brother all to himself in a private setting, he wasn't going to let anyone ruin his fun, not even Dean.

“Alright, Dean, time to wakey wakey.” Sam grinned and placed a soft kiss on Dean’s shoulder before removing the clamps and then he leaned back, eagerly waiting for Dean’s response.

Dean's reaction wasn't instantly, but Sam could see Dean's eyelids flutter as the blood in Dean's nipples started to flow back and Sam felt how his own blood seemed to start singing in his veins as Dean's eyebrows furrowed and a low whine spilled over Dean's lips. Sam stepped back a step to bask in the whole scene in front of him, all the way from the twisting of Dean's legs as he tried to yank his feet up to curl into a fetal position from the buzzing, sharp pain coming from his chest. Sam observed with raised excitement how Dean wriggled his ass and how his arms strained in vain against the armbinder, how his breathing became more uneven as he gained consciousness to a world on fire.

"Wha-ah, ouch, what, fuck- what-ah-what the hell?" Dean slurred out, his voice overflown with pain and Sam had never been more happy to be alive, and how he wished he had put up a camera to capture the look on Dean's face. The terror of being unable to move, the agony from the nipple clamps finally coming off, how Dean's eyes searched around the room and the look of relief when they found Sam.

"Sa-sammy?"

Oh, Sam was jittery with glee. _"This is going to be great."_

"Hey, Dean." Sam crouched down to gently cup the side of Dean's face. "I know it's a lot to take in, but everything's gonna be just fine."

"Sammy, I can't-ah-" Dean gritted his teeth and crunched his eyes shut, probably from a wave of pain. "Why-why does my nipples feel like they are on fire? And-ah-why can't I move?"

"Sssh, it's okay Dean, I'm here. Take it easy." Sam was pleased to hear Dean be so docile, having feared for a bit that he would have had to fight Dean into submission again, but it looked like Dean's submissive side had finally started to seep in more. Which was exactly what Sam had hoped for.

"Sammy." Dean pleaded as his watery eyes tried to focus on Sam's face. "What's, ah, what's going on?"

"Dean, what's the last thing you remember?" Sam asked, swiping his thumb up and down Dean's cheek in a soothing manner, pleased with how Dean seemed to lean into his touch.

"I-, I can't, please, Sammy, help me-"

"Dean, answer my question and I'll answer yours." Sam said sternly, pinching Dean lightly as a warning, leaving a nicely pink shade on Dean's cheek and Sam wanted to drag his tongue over it, but once again, he restrained his impulses, knowing his actions would only confuse his baby brother and just add unnecessary extra time before he would get to spank Dean.

"I-" Dean swallowed, not even flinching from the pinch, clearly it wasn't enough to register over the pain still causing his nipples to throb and send spikes of fire through his body. "I remember being in the car. I remember, ah, sitting on a bench...oh."Dean stopped in his tracks, the most adorable flush showing up on his cheeks.

"You remember the fleshlight?" 

“Yea- yes.” Dean was averting his gaze now, the blush slowly seeping down onto his neck. 

“So you are aware that you didn’t complete your punishment then, right? 

“I-I didn’t?” Dean seemed to be genuinely surprised with this, but Sam was once again pleased with seeming how trusting his brother has started acting, clearly not doubting for a second Sam’s words. 

_“Well, this time it wasn’t even a lie.”_ Sam got up from his crouched position, deciding it was time to start the punishment.

“No, you didn’t, Dean, which mean you still have to receive two more punishment. But first off, you are getting punished for begging during your punishment. But I’m going to be nice and only give you fifty slaps, even if you greatly exceeded that, since you have been a good sport and haven’t asked me to untie you or started yelling.” Sam rummaged through his bag, quickly finding the item he needed to punish Dean.

“What are you… Sam, is that a hairbrush?” Dean sounded perplexed, clearly having no idea what was going on.

“Why, yes Dean, it is.” Sam answered, a smile tugging at the corner of his eyes as he gently bounced the hairbrush in his palm. “And it’s going to help me scold you for your bad behaviour today.”

“Sammy, you’re not-, AH!” Dean yelped in surprise as Sam slapped his ass without any warning, the room echoing the sharp slapping sound of the hairbrush meeting Dean’s boxer clad ass.

_“Oh, that was a great sound.”_ Sam thought, loving the rush of the slight sting he got from slapping Dean really hard. This slight side effect was one of the reason he wanted to start using a hairbrush and perhaps later only his own hand. To get a good feeling on the amount of pain he was giving out, knowing what he must be feeling, Dean was feeling in double, maybe even a higher amount. 

“Alright, Dean, start counting.” Sam said before laying out a few more smacks, enjoying himself royally with the undignified yelps and muffled whining Dean produced and the sound of the brush hitting Dean’s ass.

“Sam! Ouch, plea-ouch, please stop!” Dean begged, clearly trying to wriggle away, but there was nowhere to go and instead he just gave Sam a great show of his ass wiggling from one side to the other. 

“Dean, I’m not going to stop until you have received your punishment. And your punishment start when you start counting. I’d suggest you start soon.”

“Sam this, ah, this is not funny!” Dean tried to crank his head enough to make eye contact with Sam, but the position he was in made him unable to get more than glimpses of Sam in the corner of his eyes. 

“Well, I’m not laughing, Dean. So. Start. Counting.” Sam used slightly more power to slap Dean thrice on the same spot, noticing with great satisfaction how the area outside Dean’s boxers were turning a nice soft shade of pink. “Remember, you still have fifty slaps to receive.”

“A-ouch, Sammy- wha-” Dean was gasping, but no matter how much Sam enjoyed hearing him moan, he was getting impatient, wanting to hear some number, not wanting to hurt his own wrists or hands from spanking Dean. So Sam roughly dragged down Dean’s boxers, enjoying the view even more with them gone. 

“Alright, Dean, I’m going to help you out. Come on, repeat after me. One.” Sam calmly ordered as he slapped Dean’s ass once more, loving how he now could see Dean’s ass completely, and imagining how the slap probably hurt even more now without the boxers gone, hoping it would spur his baby brother on to start obeying him.

“Fuck! Sammy, wait a-”

“One.” Sam repeated, hitting the exact same spot, admiring how one of Dean’s ass cheeks was turning redder than the other. 

“That-sss-”

_Slap ___

__“One.”_ _

__“A-ah, wa,” Dean made an adorable little hiccup sound, before he finally obeyed in a broken sob. “One.”_ _

__“That’s it Dean, that’s good. Keep going.” Sam praised, but giving Dean no pause before handling out the next slap, not wanting to break his flow. “Two.”_ _

__“T-two.” It seemed that now that Dean had started to count, he was eager to continue, finally understanding Sam wasn’t going to stop before he reached fifty._ _

__“That’s great. Now, you continue without my help, yeah?” Sam said, smiling with satisfaction when Dean gasped out three after the next slap._ _

__After that, Sam settled into a comfortable rhythm, switching between Dean’s cheeks, making sure both halves got the same amount of attention and love from him._ _

__By twenty Dean had stopped to move around, making it easier for Sam to hit where he wanted. By thirty-three, Dean had started to cry, making his voice coming out in whimpers and his face covered in snot and tears._ _

__But he still made Sam proud by continuing to count, as clear as he could with his uncontrollable crying and uneven breathing, all the way to the end._ _

__“Fi- ah- fifty!” Dean hiccuped, tears smearing the pillow under his face as he gasped out the last number._ _

__“Good job, Dean. Now, I want you to thank me.” Sam ordered, tracing his fingers alongside the hem of Dean’s boxers, as they were still hanging around Dean’s knee, unable to go further thanks to the ropes._ _

__“Tha-thank you? Why, uh, why would I-ah!” Dean yelped as Sam groped one of Dean’s ass cheeks, admiring the heat it radiated into his palm._ _

__“For giving you the punishment you deserved, of course.” Sam stated, greedily taking in the sight of Dean’s round, soft ass, that was very much on the red side and Sam gave himself a mental pat on the back for turning Dean’s ass into such a gorgeous shade of red that would definitely remind Dean for days who was in charge._ _

__“You gotta be kidding me.” Dean snorted, a tired, almost hysterical laugh bubbling out from his throat._ _

__“What was that, Dean?” Sam punctuated his last word with a harsh slap with his hand. He felt how his heart rate speed up while slapping Dean’s bare ass with his hand. Using the brush had not been anywhere near as exhilarating as using his bare hands. Sam added in a few more, just enjoying the slight sting in his palm and the surprised yelps from Dean._ _

__“Sam, ah, no I didn’t- please-” Dean was sobbing again, once again squirming against his restraints but to no avail._ _

__“Dean, you know exactly why you are being punished, don’t you?” Sam paused his hands, allowing Dean a break to gather his thoughts._ _

__“I… yes, yes, I do.” Dean stilled, his eyes blinking rapidly in order to clear._ _

__“Then tell me.” Sam ordered, slowly dragging his hand over Dean’s bare ass, marvelling over the slight shiver he could feel there under his fingertips. “Tell me why you’re being punished.”_ _

__“Sammy?” Dean was clearly not following what Sam was trying to do, and Sam couldn’t blame him. But that didn’t mean Sam was going to stop. He needed Dean to accept and crave the punishment, to understand that Sam was the one in control and that Dean should be thankful for receiving the punishment, since they allowed him to atone for his wrongdoings. That Dean should be eager to please him, both in serving him and he should be even more eager to receive punishment when he did something that Sam didn’t approve of._ _

__“Tell me about how you’ve been a bad boy.” Sam was going on a hunch here, hoping he had read the signs right and Dean was far enough gone into submission that he would willingly go along with Sam’s fantasies._ _

__“A-a bad boy?” Dean repeated dumbly, his thighs trembling slightly from being forced to stay in a unnatural position for so long. Sam couldn’t keep himself from placing his warm hand over that gorgeous naked skin, squeezing just to feel the shaking escalate from his action._ _

__“Yes, Dean. Tell me, what did you do wrong today to deserve this punishment.” It would be easy to feed Dean his lines, to tell him exactly what to say, but Sam wanted to reach deeper, he wanted it to be Dean himself to express his feelings and thoughts. That way it would be easier to manipulate him, to teach him what actions and words would give him rewards, and which would get him more punishment._ _

__“I--” Dean swallowed and Sam allowed his baby brother a moment to think over the question without hitting him._ _

__“Yes, Dean. Tell me why my hand is red and stinging from punishing you.” Sam let go of Dean’s thigh to crouch in front of Dean’s face, holding up his hand so Dean could see how Sam’s hand was red from the spanking. Of course, the sting was probably nothing compared to the pain Dean was feeling, but that was not something Sam was going to focus on.  
“Sammy, I’m,” Dean blinked rapidly, his eyes rapidly shifting from Sam’s hand to Sam’s face, clearly trying to read in Sam’s expression. “I’m-- sorry?”_ _

__“That’s really good, Dean.” Sam praised, using the bed sheet to wipe Dean’s face clean from some snot and tears as a slight reward. “Keep going. Tell me what you are sorry for.”_ _

__“I’m sorry for--for making you spank me.” Dean closed his eyes, his breathing noticeable more even, his forehead getting less wrinkled as Sam kept praising him and cleaning his face. “I’m sorry that you have to--to help me like this. That you have to take care of me.”_ _

__“That’s great, Dean. And you know I’m only doing this to help you, right? And now I need you to help me a bit, yeah? So tell me, how have you been a bad boy today?”_ _

__“A--a bad boy?” Dean’s forehead was getting wrinkled again and he opened his eyes again, confusion and a glint of his usual defiance back in them. “Sam, I’m not a chi-ouch!”_ _

__“Dean, Dean, Dean.” Sam chided, keeping a tight grip on the hair he had yanked hard as a warning. “Do you want to get spanked some more?”_ _

__“I--” There was a tense moment of silence, but to Sam’s relief Dean cast his eyes down. “No, I don’t.”_ _

__“Well then, Dean, since I don’t either want to spank you anymore, I’m going to help you out a bit.” Sam picked up the hairbrush again, lightly tapping it against Dean’s stomach, a non-verbal warning what would happen if Dean didn’t play along. “You just answer my questions, alright?”_ _

__“O-okay.” Dean was trembling again, but Sam paid it no mind._ _

__“Well, then, Dean, do you think a good boy would yell at someone trying to help them?”_ _

__“...no.” Dean mumbled, and Sam put a bit more force to his tapping, loving the tremor in Dean’s stomach when it hit and how Dean’s breath hitched._ _

__“What was that? I couldn't hear you.” Sam resumed his light tapping, looking forward to when he had gotten some whips and ball stretchers, the whine and screams Dean would produced when he spanked his most private parts._ _

__“NO!” Dean articulated clearly, perfectly in the clear on what would happen if he answered anything else._ _

__“Well then, do you think a good boy would try to escape a punishment they deserve?”_ _

__“No!”_ _

__“Good answer Dean.” Sam praised, using his other hand to lightly cares Dean’s cheek. “Well then, last question, do you think a good boy would be grateful over getting a punishment they clearly deserved?”_ _

__“..yes?” Another harsher tap turned Dean’s slightly questioned answer to a certain one. “Yes!”_ _

__“Good job, Dean.” Sam dropped the hairbrush, using both his hands to pet and stroke Dean’s hair. “I’m so proud of you. Now all you need to do is thank me and then I’m going to get you some water, okay?”_ _

__“Okay.” Dean’s voice was rasped and Sam marveled on how sweaty the spanking had made him. It was such a great look on him, all submissive and docile in his restraints, how he clearly leaned into Sam’s touch._ _

__“Well then Dean, tell me, what have you been?”_ _

__“I have,” Sam stilled, feeling his heart rate pick up as he impatiently waited for Dean’s next word. “I have been a bad boy, Sammy. I’m so sorry, I’m so sorry. Thank you for, for helping me.”_ _

__“That’s right, Dean. Good job.” Sam let out a breath he didn’t even know he had held in, a feeling of overjoy singing in his veins as Dean finally obediently went along with his scenario. “And what happens to bad boys?”_ _

__“They get punished.”_ _

__“That’s right, Dean, they do, just like you. But do you know why?”_ _

__“Because,” the question clearly confused Dean, as he paused mid sentence, looking at Sam’s face for answers. Sam really didn’t want to feed Dean any more answers, but he guessed he should be happy with how much Dean had improved for now and cut him some slacks._ _

__“Well Dean, of course so they will learn til next time so they won’t get punished again and instead get some rewards! Wouldn’t you like to get a reward? A treat for being a good boy?”_ _

__“I--guess?”_ _

_“Well, it’s a work in progress, but I’ll take it.”_ Sam almost rolled his eyes but decided that would have to do for now. For now, it was good enough that Dean seemed to accept the term “good boy”.

__“That’s right! I’m so proud of you, Dean! Alright, I’m going to remove some of the restrains so you’ll be more comfortable, okay? Then I’ll get your water as a reward for being such a good boy” Sam praised, ruffling Dean’s hair before getting up, starting on the armbinder. Sam unclasped the armbinder all the way to Dean’s wrist, but stopped there, not risking to let Dean use his hands freely just yet. Then he made quick work of the other restraints, only leaving Dean’s hands and feet bound._ _

__“Oh yes!” Dean moaned out as he slumped on his side, finally being able to move around more and stretch his legs._ _

__“Alright, Dean, lay still while I get you some water.” Sam ordered, walking the short distance to the refrigerator to get Dean some well-needed liquid. He turned around, licking his lips and shifting his stance so his hard-on would be slightly more bearable._ _

_“Don’t rush.”_ Sam told himself, focusing on keeping his hands steady as he opened the fridge door to get a water bottle. _“Soon he’ll be begging for your cock.”_

__Sure, Sam would have loved taking Dean right there and then, enjoying the cries and begging from Dean, as Sam would slap against his red and sensitive ass, pleading for him to stop, to go slower, to stop. Saying Sammy in that broken, sweet voice that sent a shiver right through Sam every single time. But no, Sam wanted to wait until it was Dean who was begging for him to fuck him._ _

__And he had a pretty good feeling that it wasn’t long now. But until then, he was going to enjoy dealing out some more punishment. Oh, he had so much more planned for the evening.__

**Notes for the Chapter:**

> A/N: This chapter would not have happened without people commenting!! Seriously, trust me, the fact that this story keeps getting kudos and comments is one of the biggest reasons I want to continue this story and not drop it! So please keep leaving kudos and comments and I promise you, there will be a new chapter coming your way soon!! And I assure you, it’s not going to be any easier for Dean, oh trust me ;)


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